Cesium carbonate → N-{3-[4-(cyclopropylcarbamoyl)phenyl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-6-yl}pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 mg (0.23 mmol) 4-{6-bromo-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}-N-cyclopropylbenzamide in 2 mL toluene were added 88 mg (0.7 mmol) pyridine-2-carboxamide, 76 mg (0.23 mmol) caesium carbonate, 8.4 mg (0.01 mmol) 1E,4E)-1,5-diphenylpenta-1,4-dien-3-one-palladium (3:2) and 10.8 mg (0.02 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) and the mixture was heated at 140° C. for 2 h in a microwave tube. The mixture was filtered and purified by HPLC to yield 32 mg (28%) of the title compound. UPLC-MS: RT=1.32 min; m/z (ES+) 470.5 [MH+]; required MW=469.5. 1H-NMR (300 MHz, d6-DMSO): δ=9.88 (1H, s), 8.76 (1H, s), 8.73 (1H, d), 8.56 (1H, d), 8.13-8.04 (2H, m), 7.99 (2H, d), 7.88 (1H, t), 7.76 (1H, s), 7.72 (1H, d), 7.69 (1H, m), 3.31 (2H, t), 2.87 (1H, m), 2.06 (1H, m), 0.92 (2H, d), 0.69 (2H, m), 0.55 (2H, m) ppm.

Provenance & Evidence