Dichloromethane → 7-Isoquinolinecarboxylic acid, 1-methoxy-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-bromo-1-methoxyisoquinoline (520 mg, 2.2 mmol) in methanol (30 mL) was added sodium acetate (517 mg, 6.30 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (257 mg, 0.315 mmol). The mixture was evacuated and backfilled with nitrogen three times. The reaction vessel was then pressurized to 25 psi carbon monoxide. The reaction was heated to 70° C. and was agitated for 20 hours. The reaction was filtered, rinsing with methanol. The filtrate was concentrated. The resulting residue was taken up in dichloromethane and the remaining solids were filtered off. The filtrate was concentrated and purified by flash column chromatography (0-100% ethyl acetate/heptanes) to give the title compound (443 mg, 93%) as a white solid. +ESI (M+H) 218.1; 1H NMR (400 MHz, DMSO-d6, δ): 8.77 (d, J=0.8 Hz, 1H), 8.20 (dd, J=8.6, 1.8 Hz, 1H), 8.13 (d, J=5.9 Hz, 1H), 8.00 (d, J=8.6 Hz, 1H), 7.46 (d, J=5.9 Hz, 1H), 4.08 (s, 3H), 3.90 (s, 3H).

Provenance & Evidence