Potassium Carbonate → N-cyclopropyl-3-(7-methoxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

N-allyl-2-bromo-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-methoxybenzamide (1.03 g), tri-o-tolylphosphine (283 mg), tetraethylammonium bromide (977 mg) and potassium carbonate (1.3 g) were suspended in DMF (36 ml) under argon. Pd(OAc)2 (104 mg) was added and the mixture was heated at 120° C. for 17 hours and then allowed to cool. The reaction mixture was diluted with ethyl acetate and washed with water (×5), brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting using a gradient of 50% ethyl acetate/iso-hexane to 100% ethyl acetate/iso-hexane to yield N-cyclopropyl-3-(7-methoxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a pale yellow foam (265 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.11 (s, 3H), 2.27 (s, 3H), 2.86 (m, 1H), 3.89 (s, 3H), 7.10 (s, 1H), 7.46-7.51 (m, 2H), 7.71-7.76 (m, 3H), 7.87 (d, 1H), 8.46 (d, 1H); Mass Spectrum: M+H+ 363.

Provenance & Evidence