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

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Reaction Steps

To a solution of 2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-amine (Description 62) (1.351 g, 5.25 mmol) in THF (10 mL) was added 3-chlorobenzenesulfonyl chloride (1.11 mL, 7.88 mmol), sodium tert-butoxide (1.262 g, 13.13 mmol) and the mixture stirred at RT for 16 h. The mixture was then evaporated to dryness and the resulting material taken-up in water (10 mL) and extracted with ethyl acetate (20 mL×3). The organics were then combined, dried (phase separation cartridge) and concentrated. Purification on silica, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, followed by MDAP (acidic conditions), afforded the title compound (380 mg). LCMS (A) m/z: 431/433 [M+1]+, Rt 1.22 min (acidic).

Provenance & Evidence