3-Chlorobenzenesulphonyl chloride → N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

Participants

Reaction Steps

Alternatively, to a stirred solution of 2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno-[2,3-b]pyridin-4-amine (460 mg, 1.317 mmol) (Description 17) in DMF (10 mL) was added sodium tert-butoxide (316 mg, 3.29 mmol) and 3-chlorobenzenesulfonyl chloride (0.371 mL, 2.63 mmol). The reaction mixture was stirred at RT under nitrogen for 1 h. The reaction mixture was then diluted with ethyl acetate (25 mL) and NaHCO3 (50 mL). The organic layer was then separated and the aqueous layer re-extracted with ethyl acetate (2×20 mL). The combined organic layer was dried over Na2SO4 and the solvent concentrated in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in cyclohexane, afforded the title compound (447 mg).

Provenance & Evidence