Triethylamine → N-(3-chloro-4-fluorophenyl)-4-methyl-3-(3-(pyridin-3-yl)acrylamido)benzamide

Participants

Reaction Steps

To a solution of the product of step 2 (0.7 g) and anhydrous triethylamine (0.7 ml) in dichloromethane (20 ml), 3-pyridin-3-ylacryloyl chloride hydrochloride (1.2 g) was added in batches in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for 30 min in an ice-bath, and then at room temperature overnight. The completion of reaction was indicated by TLC. Then potassium carbonate solution (10%) was added. The mixture was extracted with EtOAc (20 ml*3). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to recover solvent. The residue was purified on silica gel column using EtOAc/petroleum ether/ethanol (2:1:5) as an eluent. The concentration of the eluent and crystallization provided a yellow solid powder.

Provenance & Evidence