Ethyl Acetate → 3-Chloro-N-(3-{3-[(dimethylamino)methyl]phenyl}-2,6-dimethylthieno[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-chlorobenzene sulfonamide (Example 61) (80 mg, 0.185 mmol) was dissolved in 1,4-dioxane (1.5 mL) and water (0.5 mL). N,N-Dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine hydrochloride (83 mg, 0.278 mmol), tetrakis(triphenylphosphine)palladium(0) (21.41 mg, 0.019 mmol) and potassium carbonate (51.2 mg, 0.371 mmol) were added and heated in a microwave at 120° C. for 15 min. Ethyl acetate (10 mL) was added and washed with water (2×5 mL). The organic layer was dried over MgSO4, filtered and solvent removed in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-20% 2M NH3 in MeOH in DCM, to give the title compound (15.3 mg). LCMS (A) m/z: 486 [M+1]+, Rt 0.92 min (acidic).

Provenance & Evidence