Ethyl Acetate → 3-Chloro-N-[2,6-dimethyl-3-(5-methyl-2-thienyl)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 (Example 61) (100 mg, 0.232 mmol) was dissolved in 1,4-dioxane (1.5 mL) and water (0.7 mL). (5-Methyl-2-thienyl)boronic acid (49.3 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 10 min (×2). Ethyl acetate (10 mL) was added and the mixture washed with water (2×5 mL). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane and then further purified by MDAP (acidic conditions), to give the title compound (16 mg). LCMS (A) m/z: 449 [M+1]+, Rt 1.54 min (acidic).

Provenance & Evidence