N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine → 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-N,6-dimethoxy-benzamide

Participants

Reaction Conditions

Reaction Steps

(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (34.1 mg, 0.06 mmol), diacetoxypalladium (7.93 mg, 0.04 mmol), 2-amino-N,6-dimethoxybenzamide (131 mg, 0.67 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were weighed out in a µwave vial, sealed and dioxane (5 mL) was added. Argon was let to bubble in the mixture for 5 minutes. The reaction was stirred at 90 °C overnight. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane and MeOH, silica gel was added and the mixture was concentrated. The crude product was purified by flash chromatography on silica gel (25g) eluting with 0 to 5% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness. The residue was triturated in diethyl ether (gummy in tBuOMe) and the resulting precipitate was collected by filtration, washed with diethyl ether and dried to a constant weight to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N,6-dimethoxybenzamide (131 mg, 74.1 %) as a off-white solid.

Provenance & Evidence