Ethyl Acetate → 3-Chloro-N-[2,6-dimethyl-3-(3-pyridinyl)thieno[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 (100 mg, 0.232 mmol) (Example 61) was dissolved in 1,4-dioxane (1.5 mL) and water (0.7 mL). 3-Pyridinylboronic acid (42.7 mg, 0.347 mmol), tetrakis(triphenylphosphine)palladium(0) (26.8 mg, 0.023 mmol) and potassium carbonate (96 mg, 0.695 mmol) were added and the mixture heated in a microwave at 120° C. for 15 min. Ethyl acetate (10 mL) was added and the mixture washed with water (2×5 mL). The organic layer was then dried over MgSO4, filtered and the solvent removed in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 5% MeOH in DCM, was followed by further purification by MDAP (basic conditions), to afford the title compound (32.7 mg). LCMS (A) m/z: 430 [M+1]+, Rt 0.83 min (basic), Rt 0.85 min (acidic).

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