3-Chlorobenzenesulphonyl chloride → 3-Chloro-N-[3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

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Reaction Steps

To a stirred solution of 3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-amine (45 mg, 0.176 mmol) (Description 34) in DMF (1.5 mL) was added sodium tert-butoxide (42.3 mg, 0.441 mmol) and 3-chlorobenzenesulfonyl chloride (0.050 mL, 0.352 mmol). The reaction mixture was stirred at RT under nitrogen for 3 h and then diluted with ethyl acetate (20 mL) and water (30 mL). The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (2×15 mL). The combined organic layers were dried over Na2SO4 and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-100% ethyl acetate in DCM was followed by further purification by MDAP (acidic conditions), to afford the title compound (17.8 mg). LCMS (A) m/z: 430 [M+1]+, Rt 1.06 min (acidic), Rt 0.86 min (basic).

Provenance & Evidence