149793-69-1 Archives - Nitriles-buliding-blocks

15-Sep-21 News The important role of 149793-69-1

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, 3-Fluoro-5-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 149793-69-1, Recommanded Product: 149793-69-1

Synthesis of Int rmediate (1)Molecu lar Weight: 189.1 Molecu lar Weight: 276.3[00506] In a 3-neck 100 mL round-bottomed flask, 2-(dimethylamino)ethanol (2.925, 1.2 eq.) was dissolved in THF (50 mL, 10 Vol), added NaH portion wise in reaction mixture at -25C. Stirred the reaction mixture at -25C for 1 hr. Added 3-fluoro-5-(trifluoromethyl)benzonitrile (5.0 g,1.0 eq) Portion wise in reaction mixture. Reaction mixture was stirred at this temp for 2 hrs and then at RT overnight. Reaction completion was monitored on TLC using ethyl acetate: hexane (3:7) mobile phase. Reaction mixture was quenched into the ice-water slurry (250 mL) and compound was extracted in the ethyl acetate (50 mL x 3). Organic layer was washed with brine solution (50 mL x 3) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 6.5 g of crude compound, Yield (89.18%). This crude material was directly used for next step without purification. Mass: 276.3.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Continuously updated synthesis method about 149793-69-1

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, 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. Recommanded Product: 3-Fluoro-5-(trifluoromethyl)benzonitrile

Synthesis of Intermediate (1)Molecular Weig ht: 189.1 Molecular Weig ht: 302.3[00562] In a 3-neck 100 mL round-bottomed flask, 2-(pyrrolidin-l-yl)ethanol (6.7, 1.1 eq.) was dissolved in THF (50 mL, 10 Vol) and NaH (2.55 g) was added portion wise in reaction mixture -25C. Reaction mixture was stirred at -25C for 1 h. 3-Fluoro-5- (trifluoromethyl)benzonitrile (10.0 g,1.0 eq.) was added portion wise in reaction mixture. Reaction mixture was stirred at this temp for 2 h and then at RT overnight. Reaction completion was monitored on TLC using ethyl acetate: n-hexane (3:7) as mobile phase. Reaction mixture was quenched into the ice-water slurry (250 mL) and compound was extracted in the ethyl acetate (50 mL x 3). Organic layer was washed with brine solution (50 mL x 3) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 14.0 g of crude compound, Yield (87.57%). This crude material was directly used for next step without purification. Mass: 303.1.

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Analyzing the synthesis route of 149793-69-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-5-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

To an oven-dried round bottomed flask was added nBuLi (2.5 M in hexanes, 3.6 mL, 9.0 mmol, 1.1 eq) at -45 to -40 C. under N2. An Et2O solution (12 mL) of 2-bromo-6-methoxypyridine (1 mL, 8.14 mmol) was added dropwise at the above temperature. The resulting light brownish yellow solution was stirred at -40 to -35 C. for 20 min. The mixture was cooled to -78 C., an Et2O solution (3 ml) of 3-fluoro-5-trifluoromethyl-benzonitrile (1.50 g, 7.94 mmol) was added dropwise at -78 to -70 C. The resulting solution was stirred at this temperature for 1 h. Pretreated TMSCl (1.08 mL, 8.55 mmol, 1.05 eq) was added dropwise at -78 C. The mixture was allowed to warm to room temperature for 30 min, and then stirred at room temperature for 30 min. The reaction mixture was cooled back to -78 C., and benzyl magnesium chloride (4.1 ml, 8.2 mmol) was added dropwise. The resulting mixture was stirred at -78 C. for 0.8 h, and then warmed up to room temperature for 1 h. The reaction mixture was quenched by adding sat’d NH4Cl and 1N HCl, and stirred for 10 min. The resulting solution was extracted with EtOAc, washed with 1N NaOH, saturated NaHCO3, H2O, brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash chromatography (silica gel, hexanes/EtOAc) to give 1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(6-methoxypyridin-2-yl)-2-phenylethanamine as light brownish gum (1.42 g, yield: 44.7%). LC-MS ESI (10-90% MeOH in H2O with 0.1% TFA in a 4-min run), retention time=3.20 min, 391.12 (M+H); 1H NMR (400 MHz, CDCl3) delta ppm 7.73 (s, 1H), 7.47-7.57 (m, 2H), 7.11-7.21 (m, 4H), 6.99 (d, J=7.6 Hz, 1H), 6.80 (dd, J=7.6, 2.0 Hz, 2H), 6.61 (d, J=8.1 Hz, 1H), 3.93 (s, 3H), 3.92 (d, J=13 Hz, 1H) 3.40 (d, J=13 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-5-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/161685; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sources of common compounds: 3-Fluoro-5-(trifluoromethyl)benzonitrile

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference Compound 1C and ID sodium 3-(4-(pyrrolidin-l-yl)piperidin-l-yl)-5-(trifluoromethyl)benzoate and 3-(4- (pyrrolidin-l-yl)piperidin-l-yl)-5-(trifluoromethyl)anilineScheme 1: Synthesis of Reference Compound 1 (compounds 1-C and 1-D) 1-A 1-B 1 -C [0079] Reagents and conditions: (a) 4-(pyrrolidine-l-yl) piperidine, K2CO3, DMSO,800C; (b) i. 50% H2SO4, reflux; ii. NaOH, 2 steps; (c) DPPA, Et3N, DCM, rt; (d). TFA,DCM, rt.[0080] 1-B: To a stirred solution of 1-A (6.49 g, 34.2 mmol) in 50 mL of DMSO is added 4-(pyrrolidine-l-yl) piperidine (5.80 g, 37.6 mmol) and K2CO3 (5.20 g, 37.6 mmol) at room temperature. The reaction mixture is stirred at 80 0C for 1 hour. HPLC/MS test indicates the complete consumption of I- A) and a single new peak with the right mass for 1-B ([M+l] = 324).[0081] The reaction mixture is diluted with ethyl acetate and washed with water and brine. The organic solution is dried over Na2SO4 and concentrated. The crude product is used directly in the next step without further purification.

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; DANA FARBER CANCER INSTITUTE; WO2009/152356; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Extended knowledge of 149793-69-1

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Application of 149793-69-1,Some common heterocyclic compound, 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

Step l[0158] To a solution of 5-fluoro-3-(trifluoromethyl)benzenecarbonitrile (15.0 g, 79.3 mmol) in ethanol (30 ml) was added a solution of 50% hydroxylamine in water (10 ml, 151.5 mmol), and the resulting mixture was heated at 800C for 2 hours. The mixture was cooled to room temperature, solvent removed under reduced pressure, and 30 ml of water added. The suspension was sonicated and the solid filtered off, washed with water (2 x 20 ml), and dried under reduced pressure, to provide [5-fluoro-3- (trifluoromethyl)-phenyl](hydroxyimino)methylamine as a white solid. MS 223.1 (M+H).

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV THERAPEUTICS, INC.; WO2009/94028; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Introduction of a new synthetic route about C8H3F4N

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H3F4N

Synthesis of 3-(methylthio)-5-(trifluor e:[00376] In a 500-mL, 3 -neck round-bottomed flask equipped with an 100-mL pressure- equalizing addition funnel fitted with an nitrogen inlet, and a rubber septum, 3-fluoro-5- (trifluoromethyl)benzonitrile (8.0 g, 1.0 eq.), in acetone (40 mL). Sodiumthiomethoxide (3.42 g, 1.15 eq) was dissolved in water to make 21% aqueous solution and was added dropwise in 30 min at 5C temperature. The temperature of the reaction was slowly raised to RT and stirred for 3 h. Then temperature was raised to 50-60C and maintained for further 4-6 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH – dichloromethane as mobile phase and visualization with UV, SM Rf =0.40 and Product Rf = 0.25. Reaction was stirred for 3 hr at 25C and 4-6 hrs at 50-60C and reaction mixture was transparent. The reaction mass was quench by water and extracted by ethyl acetate (3×100 mL). The combined organic layer was washed with brine 50 mL and dried over sodium sulphate and evaporated on buchi rotaevaporator. The resulting crude compound (8 g) was subjected to further stage Yield (80.9 %); Mass: (ES+) 235.94 (M+l).

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; SHECHTER, Sharon; MCCAULEY, Dilara; WO2012/99807; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The important role of 149793-69-1

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Electric Literature of 149793-69-1, These common heterocyclic compound, 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, 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: General procedure for nucleophilic substitution: A solution of 3-fluoro-5-trifluoromethyl-benzonitrile (1 eq) and the corresponding amine (3eq) in DMA was stirred at 145C during 3h. NaCl(aq) was added. The product was taken off into ethyl acetate. The organic layer was washed two times with water then dried over Na2S04 and evaporated under reduced pressure to give the intermediate compounds.

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIBASE PHARMA; CHEVE, Gwenael; DAYDE-CAZALS, Benedicte; FAUVEL, Benedicte; BORIES, Cedric; YASRI, Abdelaziz; WO2014/102377; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New learning discoveries about 3-Fluoro-5-(trifluoromethyl)benzonitrile

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-5-(trifluoromethyl)benzonitrile, its application will become more common.

Synthetic Route of 149793-69-1,Some common heterocyclic compound, 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

Step 1: 3-{[3-(Dimethylamino)propyl](methyl)amino}-5-(trifluoromethyl)benzonitrile 500 mg (2.64 mmol) of 3-fluoro-5-(trifluoromethyl)benzonitrile, 338 mg (2.91 mmol) of N,N,N’-trimethylpropane-1,3-diamine and 767 mg (5.52 mmol) of potassium carbonate in 5.0 ml of DMSO were stirred at 110 C. for 8 h. The reaction mixture was then separated directly into its components by preparative HPLC (Method 12). The product fractions were freed from the solvent, the residue was suspended in ethyl acetate and the suspension was washed successively with saturated aqueous potassium carbonate solution and saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate and concentrated. This gave 290 mg (38% of theory) of the title compound. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 7.38 (s, 1H), 7.31 (s, 1H), 7.21 (s, 1H), 3.44 (t, 2H), 2.97 (s, 3H), 2.18 (t, 3H), 2.12 (s, 6H), 1.62 (quint, 2H). LC/MS (Method 3, ESIpos): Rt=0.72 min, m/z=286 [M+H]+.

Share a compound : 3-Fluoro-5-(trifluoromethyl)benzonitrile

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.

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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Fluoro-5-(trifluoromethyl)benzonitrile

Example-1: Preparation of 3-fluoro-5-(trifluoromethyl)benzamide : In 2 lit three necked round bottom flask equipped with mechanical stirrer, thermometer and an addition funnel, 3-fluoro-5(trifluoromethyl)benzonitrile (100 g) and dimethylsulfoxide (200 ml) was added at 25-35C and stirred for 20 min. To this, potassium carbonate (220 g) and hydrogen peroxide solution (140 ml) were added at 25-35C and stirred for 90 mins. After completion of reaction, water (1200 ml) was added to the reaction mass and stirred for an hour. Filtered the solid, washed with water, suck dried and then dried at 50-55C under vacuum for 6 hrs to get the title compound. Yield: 103 g.