Cesium carbonate → methyl 4-methyl-3-[7-(4-methylpiperazin-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-methyl-3-[1-oxo-7-{[(trifluoromethyl)sulfonyl]oxy} isoquinolin-2(1H)-yl]benzoate (243 mg), palladium acetate (12 mg), BINAP (69 mg), and cesium carbonate (449 mg) were placed in a reaction tube under an atmosphere of argon. Toluene (2.5 ml) was added followed by N-methylpiperazine (0.183 ml) and the reaction mixture was stirred in a sealed tube at 95° C. for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with water (2×), brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution gave methyl 4-methyl-3-[7-(4-methylpiperazin-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoate as a brown solid (189 mg); NMR Spectrum: (DMSOd6) 2.12 (s, 3H), 2.23 (s, 3H), 2.50 (m, 4H), 3.25 (m, 4H), 3.88 (s, 3H), 6.65 (d, 1H), 7.12 (d, 1H), 7.52-7.60 (m, 3H), 7.63 (d, 1H), 7.80 (s, 1H), 7.99 (d, 1H); Mass Spectrum: M+H+ 392.

Provenance & Evidence