3-Chlorobenzenesulphonyl chloride → N-[2-bromo-6-methyl-3-(3-methylphenyl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide

Participants

Reaction Steps

To a stirred solution of 2-bromo-6-methyl-3-(3-methylphenyl)thieno[2,3-b]pyridin-4-amine (Description 59) (487 mg, 1.461 mmol) in THF (10 mL) at −78° C. under nitrogen atmosphere was added LiHMDS (1M solution in THF) (1.608 mL, 1.608 mmol) and 3-chlorobenzenesulfonyl chloride (0.226 mL, 1.608 mmol). The reaction mixture was warmed to RT under a nitrogen atmosphere for ca. 1 h and was then partitioned between ethyl acetate and water (ca. 30 mL each). The aqueous layer was separated and re-extracted with ethyl acetate (ca. 30 mL) and the combined organic layer passed through a phase separator and the solvent removed in vacuo. Purification by chromatography on silica, eluting with a gradient of 0-50% ethyl acetate in cyclohexane afforded the title compound (320 mg). LCMS (A) m/z: 508/510 [M+1]+, Rt 1.60 min (acidic).

Provenance & Evidence