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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (26 g, 68.04 mmol) and 2-amino-6-methoxy-N-methylbenzamide (18.39 g, 102.06 mmol) in dioxane (300 mL) is added cesium carbonate (39.9 g, 122.47 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (3.94 g, 6.80 mmol) and diacetoxypalladium (0.764 g, 3.40 mmol). Mixture was degassed 3 times with N2 and heated to 100°C overnight. LCMS crude seems OK. Reaction was cooled to room temperature then salts were filtered and the filtrate concentrated to afford a crude compound which was purified on silica, eluting with 5% MeOH in AcOEt. Solvent were evaporated to afford a gum which finished by crystallize in 100mL of CH2Cl2. Solid was filtered and dried to a constant weight to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy- N-methylbenzamide (17.30 g, 58.5 %) as a white crystalline product. 1H NMR, purity check OK, 98% of purity.

Provenance & Evidence