3-Chlorobenzenesulphonyl chloride → 3-chloro-N-[3-(3-chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide

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Reaction Steps

To a solution of 3-(3-chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-amine (100 mg, 0.346 mmol) (Description 9) in THF (3 mL) was added potassium tert-butoxide (155 mg, 1.385 mmol) and the mixture stirred for 5 min before the addition of 3-chlorobenzenesulfonyl chloride (0.049 mL, 0.346 mmol). The mixture was then stirred for 1 h and the solvent then removed in vacuo. Ethyl acetate (10 mL) was then added and the mixture washed with water (3×10 mL). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, was followed by trituration with MeOH, to afford the title compound (67.8 mg). LCMS (A) m/z: 463 [M+1]+, Rt 1.09 min (basic), Rt 1.44 min (acidic).

Provenance & Evidence