Category: 53312-81-5

Synthetic Route of 53312-81-5, These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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.

A solution of (R)-tert-butyl [1-(2-chloro-6-propylpyrimidin-4-yl)piperidin-3-yl](methyl)carbamate (50 mg, 0.14 mmol) prepared in Preparation 28 and 5-amino-2-fluorobenzonitrile (23 mg, 0.17 mmol) in n-butanol (1 ml) was refluxed under stirring overnight. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=1/1?dichloromethane/methanol=10/1) and then dissolved in methanol. Hydrogen chloride gas was added to the solution. The reaction mixture was stirred at room temperature for 5 hours and then filtered to give 23 mg of the product as a pale yellow solid.

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; Lee, Hyun-Joo; Kim, Dong-Hoon; Kim, Tae-Kyun; Yoon, Young-Ae; Sim, Jae-Young; Cha, Myung-Hun; Jung, Eun-Jung; Ahn, Kyoung-Kyu; Lee, Tai-Au; US2013/331377; (2013); A1;,
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Synthetic Route of 53312-81-5,Some common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

Example 64i 5-(DiallyIamino)-2-fluorobenzonitriIe Allyl bromide (4.66 mL, 55.10 mmol), 5-amino-2-fluorobenzonitrile (3.00 g, 22.04 mmol) and sodium carbonate (0.942 mL, 22.48 mmol) were dissolved in ethanol (70.00 mL) and water (20.00 mL) and refluxed over night. The reaction mixture was allowed to cool to room temperature and the ethanol was then evaporated in vacuo. The remaining water mixture was extracted with diethyl ether (twice). The combined organic layers were passed through a phase separator and concentrated in vacuo. The product was purified by silica chromatography using 0% to 50% ethyl acetate in heptane to give 5-(diallylamino)~ 2-fluorobenzonitrile (3.31 g, 70% yield): 1H NMR (500 MHz, DMSO-J6) delta ppm 7.22 – 7.32 (m, 1 H), 6.91 – 7.04 (m, 2 H), 5.76 – 5.88 (m, 2 H), 5.08 – 5.22 (m, 4 H), 3.95 (d, 4 H); MS (ES+) m/z 217 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; BLID, Jan; GINMAN, Tobias; GRAVENFORS, Ylva; KARLSTROeM, Sofia; KIHLSTROeM, Jacob; KOLMODIN, Karin; LINDSTROeM, Johan; RAHM, Fredrik; SUNDSTROeM, Marie; SWAHN, Britt-Marie; VIKLUND, Jenny; VON BERG, Stefan; VON KIESERITZKY, Fredrik; WO2011/2408; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 53312-81-5,Some common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

General procedure: Under nitrogen atmosphere, dry CH2Cl2 (30 mL), amine (0.02 mol), and Et3N (0.05 mol) wereadded to a three-necked round bottom ask and stirred for 0.5 h, then chloroacetyl chloride droppedslowly and reacted for 3 h at room temperature. Then, the solution was washed with 2 mol L1hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively,then dried over anhydrous Na2SO4 and filtered. After evaporating CH2Cl2 in vacuum, the obtainedcrude product was rened by recrystallization using ethyl acetate/petroleum ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Article; Cai, Nan; Liu, Caixiu; Feng, Zhihui; Li, Xinghai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Ahmed, Wasim; Cui, Zining; Molecules; vol. 23; 4; (2018);,
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Related Products of 53312-81-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j1211] Compound 326 was synthesized from 5-amino-2- fluorobenzonitrile (47.2 mg, 0.346 mmol) which was stirred in dichloromethane (2 mE) and 0.50 mE saturated sodium bicarbonate solution at 0 C. Phosgene (20% in toluene, 0.495 mE, 0.693 mmol) was added and stirred for 30 mm. The organic layer was extracted with dichloromethane and washed with water followed by sodium bicarbonate solution. The organic layer was concentrated and redissolved in DMF (2 mE). Corresponding compound C (100 mg, 0.144 mmol) and TEA (95 IL, 0.6 93 mmol) was added and heated at 90 C. for 1 h. The crude product was purified with reverse phase colunm (water:CAN 1:1) to afford the target compound as a light brown solid (47.8 mg, 38.7%); 1H NMR (400 MHz, Chioroform-d) oe 0.92 (d, J=6.6 Hz, 3H), 1.16 (d, J=6.6 Hz, 3H), 1.25 (d, J=6.6 Hz, 3H), 1.71-1.83 (m, 1H), 2.00-2.08 (m, 1H), 2.10-2.18 (m, 2H), 2.25-2.44 (m, 2H),2.80-3.04 (m, 4H), 3.26-3.46 (m, 3H), 3.68-3.86 (m, 3H),4.38-4.69 (m, 6H), 4.78 (d, J=11.3 Hz, 1H), 4.92-5.05 (m, 1H), 5.07-5.18 (m, 1H), 5.36 (t, J=7.5 Hz, 1H), 5.77 (d, J=7.6 Hz, 1H), 6.54-6.68 (m, 3H), 7.05 (t, J=8.7 Hz, 1H), 7.39 (d, J=9.5 Hz, 1H), 7.48-7.56 (m, 1H), 7.72-7.81 (m, 1H), 8.15 (s, 1H), 8.47 (d, J=9.7 Hz, 1H); ESI-MS: [m/z+ H]=855.46.

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; St. Jude Children’s Research Hospital; Lee, Richard E.; Zhao, Ying; Jiuyu, Liu; (323 pag.)US2018/79784; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

53312-81-5, name is 5-Amino-2-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5-Amino-2-fluorobenzonitrile

To ethyl 3 -fluoro- 1 -methyl-4- [[( 1R)- 1 -methylpropyl] sulfamoyl]pyrrole-2-carboxylate(354 mg, 1.156 mmol) and 5-amino-2-fluoro-benzonitrile (201.7mg, 1.483 mmol) in dry THF(20 mL) at 0C, lithium bis(trimethylsilyl)amide in THF (4.62 mL, 4.62 mmol) was added. Themixture was stirred 1 hour at 0C. The reaction mixture was quenched with NH4C1 solution (30mL) and extracted with EtOAc (5OmL), diluted with brine (50 mL) and extracted again with EtOAc (50 mL). The combine organic layers were dried over sodium sulphate, filtered and concentrated. The residue (dissolved in 1 mL DMF) was purified by column chromatography on silica using a gradient from 10 till 100% EtOAc in heptane. The product fractions wereconcentrated and the solid residue was crystallized from 50 mL warm methanol upon addition of water. The white crystals were filtered off and dried in vacuo at 50C overnight, resulting in compound 186 (306 mg)MethodA: Rt: 1.83 minmlz: 395.1 (M-H) Exactmass: 396.11. ?H NMR (400 MHz, DMSO-d6) oe ppm 0.78 (t, J=7.4 Hz, 3 H), 1.01 (d, J=6.6 Hz, 3 H), 1.31 – 1.44 (m, 2 H), 3.06 – 3.20 (m, 1 H), 3.80 (s, 3 H), 7.47 (d, J=4.6 Hz, 1 H), 7.50 – 7.58 (m, 2 H), 7.96(ddd, J=9.2, 4.8, 2.9 Hz, 1 H), 8.17 (dd, J5.7, 2.6 Hz, 1 H), 10.31 (s, 1 H).

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 53312-81-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 9: 5- 5-(Benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrileA suspension of 2-chloro-5-benzyloxypyrimidine (2.0g, 9.074mmol), 5-amino-2- fluorobenzonitrile (1.24g, 9.074mmol), in’5,(dibenzylideneacetone)palladium(0) (415 mg, 0.45mmol), 4,5-bi5,(diphenylphosphino)-9,9-dimethylxanthene (525 mg, 0.90 mol) and cesium carbonate (5.9g, 18.1mmol) in de-gassed 1,4-dioxane (15mL) was heated at 80 C for 2 days. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by flash chromatography, using 0-5% ethyl acetate:hexane as eluent, to give 5- [5- (benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrile (2.88g) as yellow solid.Mass: (ES+) 321(M+H)+

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David; SCOPES, David; WO2011/144577; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 53312-81-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 53312-81-5 name is 5-Amino-2-fluorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Ethyl 4-[ [(1 R)-2,2-difluoro- 1 -methyl-propyl] sulfamoyl] -3 -fluoro- 1 -methyl-pyrrole-2-carboxylate (150mg, 0.42 mmol) and 5-amino-2-fluorobenzonitrile (75.9 mg, 0.54 mmol) were dissolved in THF (5 mL). Lithium bis(trimethylsilyl)amide (1.67 mL, 1 M, 1.67 mmol) was added drop wise and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was quenched with sat. NH4C1 (aq;, 5 mL). The organic layer was removed and the aqueous layer extracted with CH2C12 (2 x 5 mL). The combined organic layers were evaporated to dryness andthe residue was purified by silica gel chromatography (ethyl acetate in heptane 0 to 100% and again with ethyl acetate in heptane 0 to 60%). The desired fractions were evaporated to dryness, the resulting residue was dissolved in refluxing isopropanol (7 mL) and sonicated to afford a suspension. The white solids were filtered and washed with isopropanol (1 mL) to afford compound 317 (115 mg) as off white powder. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.07 (d,J6.8 Hz, 3 H), 1.58 (t, J19.1 Hz, 3 H), 3.45 – 3.61 (m, 1 H), 3.81 (s, 3 H), 7.48 – 7.54 (m, 1 H),7.54 (t, J9.2 Hz, 1 H), 7.96 (ddd, J9.2, 4.9, 2.6 Hz, 1 H), 8.04 – 8.37 (m, 1 H), 8.17 (dd, J=5.7, 2.6 Hz, 1 H), 10.32(br. s., 1 H). Method B: Rt: 0.98 minmlz: 431.1 (M-H)Exactmass: 432.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 53312-81-5, These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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.

General procedure: The synthesis was carried out by using the synthetic method c. To a solution of 3-aminobenzonitrile (0.603 g, 3.39 mmol)and DIPEA (1.09 g, 8.46 mmol) in dichloromethane (40 mL) was added picolinoyl chloride HCl salt (0.562 g, 3.39 mmol). The mixture was stirred for 4 h. The mixture solution was injected into a silica-gel column (40 g) andpurified by CombiFlash eluting with dichloromethane and ethyl acetate to give the product as a white solid (630.2 mg, 2.82 mmol, 83.3% yield)

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhaoda; Kil, Kun-Eek; Poutiainen, Pekka; Choi, Ji-Kyung; Kang, Hye-Jin; Huang, Xi-Ping; Roth, Bryan L.; Brownell, Anna-Liisa; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3956 – 3960;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 53312-81-5, 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 53312-81-5 as follows.

A solution of Et3N (0.179 mL, 1.29 mmol) in DMF (1.9 mL) was added to 3-fluoro-1-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]pyrrole-2-carboxylic acidIl25 mg, 0.428 mmol), HATU (204mg, 0.535 mmol), 4-fluoro-3-methylaniline (107 mg, 0.857 mmol) and stirred overnight. The solution was subjected to column chromatography using a gradient from 10 till 100% EtOAc in heptane. The product fractions were combined and concentrated. Compound 94 (78 mg) was obtained as a white powder after drying in vacuo at 50C.J=4.8 Hz, 1 H), 8.56 (d, J=8.8 Hz, 1 H), 13.13 (br. s., 1 H). Compound 170 (531 mg) was synthesized similarly as described for compound 94 using 3-fluoro-1-methyl-4-[[(1R)-2,2,2- trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid (601.7 mg 1.89 mmol) instead of 3 -fluoro- 1 -methyl-4- [(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid and 5 -amino-2-fluorobenzonitrile (531 mg, 3.78 mmol) instead of 4-fluoro-3 -methylaniline and the reaction mixture was stirred overnight at 65C. The column fractions were concentrated and the residue was crystallized by dissolving in 100 mL warm methanol upon addition of water. The crystals were filtered off and dried overnight in vacuo at 50C. Method A: Rt: 1.66 mm mlz: 435 (M-H) Exact mass: 436.06.?H NMR (400 MHz, DMSO-d6) oe ppm 1.18 (d, J=6.8 Hz, 3 H), 3.81 (s, 3 H),3.91 – 4.05 (m, 1 H), 7.50 – 7.59 (m, 2 H), 7.96 (ddd, J=9.2, 5.0, 2.8 Hz, 1 H), 8.17 (dd, J=5.8,2.8 Hz, 1 H), 8.62 (d, J=8.8 Hz, 1 H), 10.36 (s, 1 H). Differential scanning calorimetry: From 30 to 300 C at 10C/mm: peak at 190.99 C.

According to the analysis of related databases, 53312-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts