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