Electric Literature of 1111637-68-3, 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 1111637-68-3 as follows.
To a solution of 5-bromo-3-fluoro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.65mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.77 g, 6.98 mmol), potassium acetate (1.37 g, 13.95 mmol) and l, l’-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (340 mg, 0.46mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (240 mg, 20%): NMR (400 MHz, Chloroform-d) delta 11.44 (m, 1H), 8.73 (d, 7= 1.6 Hz, 1H), 8.46 (d, 7= 1.2 Hz, 1H), 7.10 (m, 1H), 1.39 (s, 12H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-68-3, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
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