Category: 796600-15-2

Synthetic Route of 796600-15-2, A common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Examples 11 and 12Example 11 Example 12 11a to l ib(R)-2-(3 -chloro-4-cyano-2-methylphenylamino)-3 -hydroxypropanoic acidTo a stirred solution of 2-chloro-4-fluoro-3-methylbenzonitrile (1 la) (1.0 gm, 5.8 mmol) in DMSO (10 mL), D-Serine (1.4 gm, 13.3 mmol) was added followed by K2C03 (1.7 gm, 12.3 mmol) at room temperature. The resulting reaction mixture was heated to 90C for 12 h. After completion of reaction (by TLC), the reaction mixture was poured into ice-cold water (300 mL) and extracted with EtOAc (100 mL). The aqueous layer was acidified with citric acid (pH ~3) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over Na2S04, and concentrated under reduced pressure to afford the acid 1 lb (0.3 gm, crude) as off- white solid. The crude material was taken for the next step without purification.TLC: 10% MeOH/DCM (Rf: 0.2)1H NMR (500MHz, DMSO-c¾, delta in ppm): 8.2-10.2 (br s, 1H), 7.54 (d, J= 8.5 Hz, 1H), 6.57 (d, J= 9.0 Hz, 1H), 5.79 (d, J= 7.5 Hz, 1H), 4.20 (t, J= 3.0 Hz, 1H), 3.86-3.79 (m, 2H), 3.22 (br s, 1H), 2.25 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; RADIUS HEALTH, INC.; MILLER, Chris, P.; WO2012/47617; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 796600-15-2, The chemical industry reduces the impact on the environment during synthesis 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

Heat 2-chloro-4-fluoro-3-methyl-benzonitrile (144 mg, 0.85 mmol) and 2- . phenyl-pyrrolidine (0.15 g, 1.02 mmol, 1.20 equivalents) in N-methylmorpholine (0.11 ml, 1.02 mmol, 1.20 equivalents) at 150 0C overnight. Allow the reaction mixture to cool to room temperature, dilute with dichloromethane (1 ml), load on silica, and purify by chromatography (12 g silica gel, 0 to 100% ethyl acetate/hexanes over 20 minutes) to obtain 150 mg of an oily residue. Recrystallize from ethyl acetate/hexanes to obtain the title compound (92 mg, 37%). LCMS(APCI+): 297.0 (M+l)+; 1H NMR (400 MHz, CDCl3): delta 7.25 (s, 2H), 7.19 (m, 2H), EPO 6.65 (d, IH), 4.70 (m, IH), 4.06 (m, IH), 3.18 (m, IH), 2.44 (m, IH), 2.43 (s, 3H), 2.12 (m, IH), 1.94 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-4-fluoro-3-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 796600-15-2

Example 38; DL-Threo-2-chloro-4-(2-hydroxy-2-phenyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethylamino)-3-methylbenzonitrile; Intermediate 38a; DL-Threo-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxy-3-phenylpropanoic acid; 2-chloro-4-fluoro-3-methylbenzonitrile (2.0 g, 11.79 mmol) was mixed together with DL-Threo-3-phenylserine hydrate (2.82 g, 14.15 mmol) in DMSO (15 mL). K2CO3 (3.26 g) was added to the reaction mixture and stirred at 75 C. for 24 h. The reaction mixture was cooled to room temperature and poured slowly into a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed with a gradient of hexanes/EtOAc and then with EtOAc, 100% to get the pure final product (800 mg). 1H NMR (500 MHz, acetone-d6, delta in ppm) 7.52 (m, 3H), 7.37 (d, J=9 Hz, 1H), 7.2-7.30 (m, 2H), 6.81 (d, J=9 Hz, 1H), 6.44 (d, J=6 Hz, 1H), 5.42 (m, 1H), 4.5 (br s, 1H), 4.17 (m, 1H) 2.24 (s, 3H)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Miller, Chris P.; US2009/253758; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H5ClFN

Example 79; (R)-2-chloro-4-(1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-3-hydroxypropylamino)-3-methylbenzonitrile; Intermediate 79a; (R)-2-(3-chloro-4-cyano-2-methylphenylamino)-4-hydroxybutanoic acid; To a suspension of D-Homoserine (2.5 g, 20.99 mmol) and K2CO3 (5.8 g, 41.98 mmol) in DMSO (30 mL) was added 2-chloro-3-methyl-4-fluorobenzonitrile (3.56 g, 20.99 mmol) at room temperature. The reaction mixture was heated to 80 C. and stirred for 17 h. The reaction mixture was allowed to cool to room temperature and quenched with H2O (200 mL) and extracted with EtOAc (3×200 mL). The aqueous layer was then acidified with solid citric acid and extracted with EtOAc (2×100 mL). The organic extracts were combined, washed with H2O (3×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provided the title compound as a beige solid (3.39 g, 60%): 1H NMR (400 MHz, delta in ppm) 7.49 (d, J=9 Hz, 1H), 6.62 (d, J=9 Hz, 1H), 6.06 (br d, J=9 Hz, 1H), 4.49-4.41 (m, 1H), 3.83-3.80 (m, 2H), 2.29 (s, 3H), 2.27-2.20 (m, 1H) and 2.18-2.09 (m, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Miller, Chris P.; US2009/253758; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 796600-15-2

Heat a mixture of 2,4-dihydroxy-4-phenyl-l -butylamine (1.8 g, 10 mmol) and 2-chloro-4- fluoro-3-methyl-benzonitrile (1.0 g 6 mmol), cesium carbonate (4.Og, 12 mmol) and anhydrous dimethyl sulphoxide (10 ml) at 100 0C for 5 h. Allow the reaction cool and partition between ethyl acetate (100 ml) and water (3 x 50 ml). Wash the organic layer with 1.0M hydrochloric acid, dry over magnesium sulphate and concentrate to give a yellow oil (1.0 g). Dissolve this material in dichloromethane (20 ml) and treat with trifluoroacetic acid (5 ml). Allow the reaction mixture to stand at room temperature overnight and then wash with water (20 ml) and 2.0M sodium hydroxide (20 ml). Dry the organic layer over EPO magnesium sulphate and concentrate to dryness. Purify the residue by silica gel chromatography (eluting with 5 to 10% methanol / dichloromethane) to give 50 mg (1.6% yield as a single diastereoisomer) of the title compound as a white solid. MS: 313 [M C135+H]+ and 335 [M Cl35+Na]+; 1H NMR (300 MHz, CDCl3): delta 7.28 (m, 5H), 7.20 (d, IH), 6.72 (d, IH), 5.09 (m, IH), 4.60 (br m, IH), 4.29 (m, IH), 3.10 (m, IH), 2.44 (m, IH), 2.43 (s, 3H), 2.00 (m, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 796600-15-2, its application will become more common.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-4-fluoro-3-methylbenzonitrile

Example 22-Chloro-4-[[(lS,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrilebsoluteIn a sealed pressure vessel, a mixture of 2-chloro-4-fluoro-3-methyl-benzonitrile (1.2 g, 7.08 mmol), (lR,2S)-2-amino-l-methyl-cyclopentanol (1.63 g, 14.2 mmol) and lithium carbonate (1.10 g, 14.9 mmol) in DMSO (14.4 mL) and water (1.4 mL) is heated at 130 C overnight. After allowing the reaction to cool to room temperature, the mixture is diluted with EtOAc and washed twice with 1 N hydrochloric acid. The organic phase isconcentrated under reduced pressure and purified using radial chromatography eluting with EtOAc/hexanes (20 to 50% EtOAc/hexanes gradient). The resulting residue is repurified using radial chromatography with 1% methanol/dichloromethane. The isolated product is recrystallized with ether/hexanes, collected by filtration, and dried under reduced pressure to yield the title compound as a white solid (450 mg, 24%). A second crop (84 mg) is also isolated. LC-ES/MS m/z (35C1/37C1) 265/267 (M+l). 1H NMR (400 MHz, DMSO-d6) delta 1.16 (s, 3H), 1.71-1.73 (m, 5H), 2.12-2.13 (m, 1H), 2.14 (s, 3H), 3.46-3.50 (m, 1H), 4.93 (s, 1H), 5.26-5.30 (m, 1H), 6.63 (d, J= 8.8 Hz, 1H), 7.47 (d, J= 8.6 Hz, 1H). Chiral HPLC showed the material had an enantiomeric excess of 67%. The enantiomeric excess is determined by SFC on a CHIRALPAK AS-H (4.6 x 150 mm, 5 mupiiota) column using 20% ethanol/carbon dioxide. Flow rate: 5 mL/min. Detection: 225 nm. Isomer 1 (title compound):TR = 1.39 min; Isomer 2: TR = 1.99 min. The absolute stereochemistry of Isomer 1 (1S,2R) is known by correlation of retentions times with Isomer 1 and Isomer 2 as described inExample 3.The enantioenriched material (534 mg) is dissolved in methanol (5.5 mL) and purified in 500 mu?. injections by SFC on a CHIRALPAK AS-H (2.1 x 25 cm, 5 muiotaeta) column using 20% ethanol/carbon dioxide. Flow rate: 70 mL/min. Detection: 225 nm. The title compound is isolated as the first eluting peak, Isomer 1 (326 mg) in 99% enantiomeric excess. The enantiomeric excess is determined by SFC as described above.

The synthetic route of 796600-15-2 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 796600-15-2, A common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Examples 11 and 12Example 11 Example 12 11a to l ib(R)-2-(3 -chloro-4-cyano-2-methylphenylamino)-3 -hydroxypropanoic acidTo a stirred solution of 2-chloro-4-fluoro-3-methylbenzonitrile (1 la) (1.0 gm, 5.8 mmol) in DMSO (10 mL), D-Serine (1.4 gm, 13.3 mmol) was added followed by K2C03 (1.7 gm, 12.3 mmol) at room temperature. The resulting reaction mixture was heated to 90C for 12 h. After completion of reaction (by TLC), the reaction mixture was poured into ice-cold water (300 mL) and extracted with EtOAc (100 mL). The aqueous layer was acidified with citric acid (pH ~3) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over Na2S04, and concentrated under reduced pressure to afford the acid 1 lb (0.3 gm, crude) as off- white solid. The crude material was taken for the next step without purification.TLC: 10% MeOH/DCM (Rf: 0.2)1H NMR (500MHz, DMSO-c?, delta in ppm): 8.2-10.2 (br s, 1H), 7.54 (d, J= 8.5 Hz, 1H), 6.57 (d, J= 9.0 Hz, 1H), 5.79 (d, J= 7.5 Hz, 1H), 4.20 (t, J= 3.0 Hz, 1H), 3.86-3.79 (m, 2H), 3.22 (br s, 1H), 2.25 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; RADIUS HEALTH, INC.; MILLER, Chris, P.; WO2012/47617; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 796600-15-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Heat a slurry of 2-chloro-4-fluoro-3-methyl-benzonitrile (0.4 g, 2.36 mmol) and L-proline (2.11 g, 18.8 mmol) in N-methylmorpholine (1.6 mL) at 200 0C in a microwave for 30 min. Partition the reaction between 2N aqueous hydrochloric acid and ethyl acetate. Separate and extract the organic portion with 2N aqueous sodium hydroxide. Acidify the aqueous extract to pH 1 by adding concentrated EPO hydrochloric acid and back extract into ethyl acetate. Extract the combined organic portions with brine, dry over magnesium sulphate, filter, and concentrate under reduced pressure to give the title compound. (0.395 g, 63%) mass spectrum (m/e): 263(M-I); 1H NMR (300 MHz, CDCl3): delta 8.66(bs,lH0, 7.31(d, IH), 6.75(d, IH), 4.38(t,lH), 3.67(m, IH), 3.10(m,lH), 2.43(m,lH), 2.29(s,3H), 2.20-1.90(m.3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-3-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 796600-15-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 796600-15-2 as follows.

Example 1tra/?s-2-Chloro-4-[ [2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile, Isomer 2bsoluteIn a glass pressure vessel, a mixture of trans-2-amino-l-methyl-cyclopentanol (8.75 g, 53 mmol, 1.5 eq), 2-chloro-4-fluoro-3-methyl-benzonitrile (6 g, 35.4 mmol) and lithium carbonate (7.84 g, 106 mmol) in DMSO (72 mL) and water (7.2 mL) is degassed for 15 min by bubbling nitrogen through the mixture. The vessel is sealed and heated at 130 C for 36 h. After cooling to room temperature, the mixture is quenched over ice/water (700 mL) at 5 C (internal temperature) with stirring. After 15 min, the initially sticky solid turns into a cream solid that is collected by filtration and washed with cold water. The solid is stirred over EtOAc (100 mL) for 30 min and filtered through a pad of diatomaceous earth. The EtOAc filtrate is concentrated to afford 15 g of a yellow solid. The material is purified by silica gel chromatography using dichloromethane to elute impurities and 10%EtOAc/dichloromethane to elute final product to obtain the racemic title compound (9.2 g, 98%). 1H NMR (400 MHz, DMSO-d6) delta 7.48 (d, 1H), 6.90 (d, 1H), 5.51 (d, 1H), 4.66 (s, 1H), 3.65-3.74 (m, 1H), 2.21 (s, 3H), 2.01-2.13 (m, 1H), 1.50-1.78 (m, 5H), 1.07 (s, 3H). LC-ES/MS m/z (35C1/37C1) 265.2/267.1 (M+l). The compound is dissolved in MeOH (70 mL). The enantiomers are separated in 21 mg injections by supercritical fluid chromatography on two CHIRALPAK AD-H columns (2 x 25 cm, 5 muiotaeta) stringed in series. Mobile phase: 20% isopropanol/carbon dioxide. Flow rate: 65 mL/min. Detection: 215 nm. Each run is 6.48 min. The first eluting peak is obtained as Isomer 1 and the second eluting peak is obtained as the title compound, Isomer 2 (4.13 g, 100% enantiomeric excess). The enantiomeric excess is determined by SFC on a CHIRALPAK AD-H (4.6 x 100 mm, 5 muiotaeta) column using 20% isopropanol/carbon dioxide. Flow rate: 2.5 mL/min. Detection: 215 nm. Isomer 1 TR = 2.53 min. Isomer 2 (title compound) TR = 3.06 min.The compound of Example 1 can also be named or referred to as 2-chloro-4- [ [( 1 R,2R)-2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile.

According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 796600-15-2 as follows. Quality Control of 2-Chloro-4-fluoro-3-methylbenzonitrile

Example 58; (R)-2-Chloro-4-(1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethylamino)-3-methylbenzonitrile; Intermediate 58a; (R)-2-(3-Chloro-4-cyano-2-methylphenylamino)-3-hydroxypropanoic acid K2CO3 (5.71 g, 41.28 mol) was added to a solution of 2-chloro-4-fluoro-3-methylbenzonitrile (3.5 g, 20.64 mmol) and D-Serine (2.17 g, 20.096 mol) in DMSO (100 mL) at room temperature. The reaction mixture was heated to 75 C. and stirred for 19 h, then was allowed to cool to room temperature whereupon water (30 mL) was added followed by citric acid monohydrate (5g). After stirring for 10 min the mixture was partitioned between EtOAc (50 mL) and water. The organic phase was then washed with water (20 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated to furnish a pale yellow solid (4.2 g). This crude product was then passed through a silica-plug [hexanes-EtOAc (95:5) as eluent] to furnish the title compound as a white solid (1.5 g, 29%) 1H NMR (500 MHz, acetone-d6, delta in ppm) 7.49 (d, J=9 Hz, 1H), 6.72 (d, J=9 Hz, 1H), 5.56 (d, J=8 Hz, 1H), 4.43-4.40 (m, 1H), 4.06 (dd, J=11, 18 Hz, 1H), 4.05 (dd, J=11, 18 Hz, 1H) and 2.31 (s, 3H).

According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Miller, Chris P.; US2009/253758; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts