Cesium carbonate → 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-6-methoxy-N-methyl-benzamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-amino-6-methoxy-N-methylbenzamide (2.48 g, 13.8 mmol), N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (2.63 g, 6.88 mmol), palladium(II) acetate (0.077 g, 0.34 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.398 g, 0.69 mmol) and cesium carbonate (4.48 g, 13.77 mmol) in dioxane (37 mL) was degassed with argon and stirred at 100° C. for 3 hours. The reaction mixture was concentrated to dryness, diluted with EtOAc (80 ml), washed with water (1×50 ml) and brine, dried over magnesium sulfate and concentrated to afford an oil. The crude product was purified by flash chromatography on silica gel eluting with EtOAc and then 3 to 8% MeOH in EtOAc. The solvent was evaporated to dryness to afford a foam which was dissolved in DCM (12 ml). A solid formed after a few minutes and this was filtered and dried to give the title compound as a white solid (1.570 g, 52.5%). 1H NMR spectrum (500 MHz, CDCl3): 2.15 (s, 3H), 2.97 (d, 3H), 3.79 (s, 3H), 3.91 (s, 3H), 5.99 (s, 1H), 6.32 (s, 1H), 6.56 (d, 1H), 7.05 (d, 1H), 7.20 (dd, 1H), 7.34 (s, 1H), 7.44 (q, 1H), 8.23 (s, 1H), 10.56 (s, 1H); Mass spectrum: ESI+435.

Provenance & Evidence