Cesium carbonate → 3-Chloro-N-{2-(3,5-dimethyl-4-isoxazolyl)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (100 mg, 0.191 mmol) (Example 33), (3,5-dimethyl-4-isoxazolyl)boronic acid (40.4 mg, 0.286 mmol), palladium(II) acetate (4.29 mg, 0.019 mmol), xantphos (22.09 mg, 0.038 mmol) and Cs2CO3 (187 mg, 0.573 mmol) were weighed into a round bottom flask. Degassed toluene (2 mL) was added to the mixture which was then heated at 110° C. for 19 h. After cooling to RT, the mixture was filtered through celite and rinsed with ethyl acetate (30 mL) and the combined filtrate concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in isohexane, afforded the title compound (19 mg). LCMS (A) m/z: 540 [M+1]+, Rt 1.40 min (acidic), Rt 0.94 min (basic).

Provenance & Evidence