Diisopropylethylamine → 2,6-difluoro-N-(5-(2-methyl-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)pyridin-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (9.4 mg, 53 μmol) was added to a stirred solution of 240 (6.5 mg, 26 μmol) and Hünig's base (28 μL, 21 mg, 0.2 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (0.6 mL), methanol (0.4 mL) and 2 M sodium hydroxide solution (0.2 mL). The mixture was stirred and heated to 60° C. for 5 min then cooled to room temperature, diluted with dichloromethane (5 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 236 (5.1 mg, 50%) as a solid: LRESIMS m/z 385.1 [M+H]+, calcd. for C21H19F2N2O1S1 385.1.

Provenance & Evidence