Category: 127510-96-7

Application of 127510-96-7, These common heterocyclic compound, 127510-96-7, name is Methyl 2-cyano-4-fluorobenzoate, 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.

Into a 100-mL round-bottom flask, was placed methyl 2-cyano-4-fluorobenzoate (3.58 g, 19.983 mmol, 1 equiv), (piperidin-4-yl)methanol (3.45 g, 29.954 mmol, 1.50 equiv), DIEA (9.9 mL, 56.837 mmol, 2.84 equiv), DMSO (40 mL). The resulting mixture was stirred for 2h at 110 in an oil bath. The reaction mixture was cooled to room temperature and diluted with water (200 mL). The resulting mixture was extracted with ethyl acetate (200 mL x 2) and the organic layers combined. The combined organic layers were washed with brine (200 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/1). This resulted in 5.21 g (95%) of methyl 2-cyano-4-[4-(hydroxymethyl)piperidin-1-yl]benzoate as a yellow green semi-solid. LC/MS (ESI) m/z: 274.95 [M+1] +.

Statistics shows that Methyl 2-cyano-4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 127510-96-7.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; DONG, Hanqing; QIAN, Yimin; ZIMMERMAN, Kurt; (1451 pag.)WO2020/51564; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 127510-96-7,Some common heterocyclic compound, 127510-96-7, name is Methyl 2-cyano-4-fluorobenzoate, molecular formula is C9H6FNO2, 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 9a) 2-Cyano-4-dimethylamino-benzoic acid methyl ester (9a)To a stirred solution of 4,03 g (22.5 mmol) 2-Cyano-4-fluoro-benzoic acid methyl ester (J. Med. Chem., 35; 24; (1992); 4613-4627) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 9h at 600C in an autoclave and was concentrated with high vacuum rotation evaporator at 65C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 9a was obtained in 85% yield (3,90 g, 19.1 mmol). MS-ESI: 205 (M+ +1 , 81).Elementary analysis: C 64.69% H 5.92% N 13.72%Determined: C 64.72% H 5.95% N 13,70%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-cyano-4-fluorobenzoate, its application will become more common.

Synthetic Route of 127510-96-7,Some common heterocyclic compound, 127510-96-7, name is Methyl 2-cyano-4-fluorobenzoate, molecular formula is C9H6FNO2, 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: 5-(3-(3-(3-((1r,3r)-3-((5-(5H-pyrido[4,3-b]indol-7-yl)-3-(trifluoromethyl)pyridin-2-yl)oxy)cyclobutoxy)propoxy)propoxy)azetidin-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione A mixture of 7-(6-((1r,3r)-3-(3-(3-(azetidin-3-yloxy)propoxy)propoxy)cyclobutoxy)pyridin-3-yl)-5-methyl-5H-pyrido[4,3-b]indole (crude, 0.390 mmol) [prepared as described for Compound 104], N-ethyl-N-isopropylpropan-2-amine (86 mg, 1.17 mmol) and methyl 2-cyano-4-fluorobenzoate (90 mg, 0.468 mmol) in 1-methyl-2-pyrrolidinone (3 ml) was stirred at 90 C. for 16 hour. TLC showed the reaction was complete. The reaction mixture was partitioned between ethyl acetate (20 ml) and water (30 ml). The organic layer was collected, washed with brine (20 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash column chromatography (eluted with 2-4% methanol in dichloromethane) to afford 5-(3-(3-(3-((1r,3r)-3-((5-(5H-pyrido[4,3-b]indol-7-yl)-3-(trifluoromethyl)pyridin-2-yl)oxy)cyclobutoxy)propoxy)propoxy)azetidin-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (160 mg, yield 61%) as light yellow oil.

The synthetic route of 127510-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts