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

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Reaction Steps

To a solution of 3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine (1.6 g, 6.22 mmol) (Description 8) in THF (30 mL) was added potassium tert-butoxide (2.79 g, 24.89 mmol) and the mixture stirred for 5 min before adding 3-chlorobenzenesulfonyl chloride (2.190 mL, 15.56 mmol). The mixture was stirred for 1 h and the solvent was then removed in vacuo. Ethyl acetate (50 mL) was added and the mixture washed with water (3×30 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, afforded the title compound (1.3 g). LCMS (A) m/z: 431/433 [M+1]+, Rt 1.38 min (acidic).

Provenance & Evidence