2-Chloro-4-iodo-5-(trifluoromethyl)pyridine → 2-(2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

2-chloro-4-iodo-5-(trifluoromethyl)pyridine (7 g, 22.77 mmol), 2-amino-6-methoxy-N-methylbenzamide (4.31 g, 23.91 mmol), diacetoxypalladium (0.409 g, 1.82 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.108 g, 3.64 mmol) and cesium carbonate (8.90 g, 27.32 mmol) were suspended in dioxane (75 ml). Argon was let to bubble into the dark purple blurred solution and the reaction mixture was heated to at 90 °C for 24h. (yellow suspension when temperature reached 70°C). The reaction mixture was allowed to cool to room temperature, diluted with DCM (some drop of MeOH) and filtered. Silica gel was added and solents were evaporated to afford the crude, which was purified twice* by flash chromatography on silica gel eluting with 10 to 60% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide (7.00 g, 85 %) as an yellow foam.

Provenance & Evidence