Dichloromethane → 3-chloro-N-(2,6-dimethyl-3-phenylthieno[2,3-b]pyridin-4-yl)benzenesulfonamide

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Reaction Conditions

Reaction Steps

Under nitrogen, N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (90 mg, 0.208 mmol) (Example 61) was dissolved in 1,4-dioxane (3 mL). Phenylboronic acid (38.1 mg, 0.313 mmol), PdCl2(dppf).DCM (17.02 mg, 0.021 mmol) and Cs2CO3 (204 mg, 0.625 mmol) were added and the mixture heated in a microwave at 120° C. for 30 min. Toluene (3 mL) was added and the mixture heated in a microwave as follows: 130° C. for 30 min, 150° C. for 30 min (×2) and finally 180° C. for 15 min (×2). Water (10 mL) was then added and the mixture extracted with ethyl acetate (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 further purification by MDAP (basic conditions), to afford the title compound (14.4 mg). LCMS (A) m/z: 429 [M+1]+, Rt 1.10 min (basic), Rt 1.47 min (acidic).

Provenance & Evidence