6-azaindole-7-carboxylic acid Methyl ester synthesis

Yield:945840-73-3 84%

Reaction Conditions:

with triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in toluene at 110; under 37503.8 Torr; for 17 h;

Steps:

E1

EXAMPLE E1 Preparation of 1H-pyrrolo[2,3-c]pyridine-7-carboxylic acid methyl ester (E1.1) A solution of 7-chloro-1H-pyrrolo[2,3-c]pyridine (J. Org. Chem. 2002, 67, 2345; 200 mg, 1.31 mmol), triethylamine (549 mg, 5.43 mmol), and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (54 mg, 66 μmol) in methanol (3 mL) and toluene (3 mL) was stirred for 17 h at 110° C. under a carbon monoxide atmosphere (50 bar). After cooling and evaporation of volatile material, the residue was chromatographed (SiO₂, heptane/ethyl acetate gradient), to afford the title compound (194 mg, 84%). Off-white solid, MS (EI) 118.1 (100), 146.1 (26), 176.2 (35, M⁺).

References:

US2007/185154,2007,A1 Location in patent:Page/Page column 10