Category: 1150618-36-2

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1150618-36-2, name is 5-Bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H4BrF3N2, molecular weight is 265.03, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

To a solution of 5-bromo-3-(trifluoromethyl)-lH-pyrrolo[2,3-b]pyridine (19 g, 72.3 mmol) in 1,4-dioxane (400 mL) was added potassium acetate (21.27 g, 220 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (21.9 g, 86.7 mmol). The resulting mixture was degassed with nitrogen for 5 times, l, l’-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (5.3 g, 7.23 mmol) was added and the mixture was degassed again. The reaction mixture was stirred at 80-90 C and overnight. The reaction mixture was poured into water, extracted with ethyl acetate (3 x 500mL), washed with brine, dried over sodium sulphate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200mesh, 10% to 20% ethyl acetate in petroleum ether) affording 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-lH- pyrrolo[2,3-b]pyridine (11.1 g, 49 %): NMR (400MHz, DMSO-d6), delta 12.62 (s, 1H), 8.58 (s, 1H), 8.21 (s, lH), 8.18 (s, 1H), 1.31 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1150618-36-2, 5-Bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1150618-36-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1150618-36-2, name is 5-Bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H4BrF3N2, molecular weight is 265.03, as common compound, the synthetic route is as follows.

A mixture of 5-bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.250 g, 0.943 mmol), phenylmethanethiol (0.122 mL, 1.038 mmol), DIEA (0.329 mL, 1.887 mmol), Pd2(dba)3 (43.19 mg, 47.16 mumol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (54.58 mg, 94.33 mumol) in dioxane (10 mL) was stirred for 1 hour and heated to 150 C for 2 hours under microwave conditions. The mixture was cooled to RT and taken up in EtOAc. The organic layer was washed with NaHCO3(3x) and brine, dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography (1:1EtOAc/hexane) to give the title compound as a yellow solid (0.78g, 95% yield). LCMS m/z = 309.4[M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1150618-36-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; TRAN, Thuy-Anh; ULLMAN, Brett; KRAMER, Bryan Aubrey; DO, Quyen-Quyen Thuy; SHIN, Young-Jun; (202 pag.)WO2019/113359; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem