Ethyl Acetate → HCID 68324039, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 61) (85 mg, 0.197 mmol) was dissolved in 1,4-dioxane (1.5 mL) and water (0.5 mL). 1,1-Dimethylethyl {[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamate (98 mg, 0.295 mmol), tetrakis(triphenylphosphine)palladium(0) (22.75 mg, 0.020 mmol) and potassium carbonate (54.4 mg, 0.394 mmol) were added and the mixture heated in a microwave at 100° C. for 10 min (×2). Ethyl acetate (10 mL) was then 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. The residue was purified by normal phase chromatography, eluting with a gradient of 0-30% ethyl acetate in cyclohexane and then further purified by normal phase chromatography, eluting with ethyl acetate and cyclohexane (0-30%), to give the title compound (52 mg). LCMS (A) m/z: 558 [M+1]+, Rt 1.47 min (acidic).

Provenance & Evidence