p-Bromobenzenesulfonyl chloride → 4-Bromo-N-{2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

Participants

Reaction Steps

To a solution of 2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (Description 4) (100 mg, 0.352 mmol) in THF (2 mL) cooled in an ice bath was added LiHMDS (1M solution in THF) (0.774 mL, 0.774 mmol). The resulting reaction mixture was stirred for 45 min before addition of 4-bromobenzenesulfonyl chloride (225 mg, 0.879 mmol). The reaction mixture was then stirred at RT for a further 12 h. The reaction mixture was diluted with water (15 mL) and the aqueous layer re-extracted with DCM (30 mL×3). The organics were combined, dried over a phase separating column and concentrated. To the residue was added MeOH (ca. 0.5 mL) and a solid crashed-out which was collected by filtration and rinsed with MeOH (ca. 2 mL). The solid was then dried, to afford the title compound (104 mg). LCMS (A) m/z: 503/505 [M+1]+, Rt 1.11 min (basic).

Provenance & Evidence