Potassium Carbonate → N-[3-[3,5-Bis(methyloxy)phenyl]-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl 4-(3-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridin-2-yl)-1H-pyrazole-1-carboxylate (Description 75) (100 mg, 0.171 mmol), 3,5-dimethoxyphenylboronic acid pinacol ester (90 mg, 0.343 mmol), potassium carbonate (95 mg, 0.685 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.96 mg, 3.43 μmol) were weighed into a microwave vial. 1,4-Dioxane (1.5 mL), DMF (0.75 mL) and water (0.38 mL) were added and the mixture heated in a microwave at 110° C. for 30 min. At this point, both reaction mixtures were combined and concentrated. The residue was passed through an SCX cartridge, eluting with MeOH (75 mL) and then with 2M NH3 in MeOH (100 mL). The basic methanolic solution was concentrated and purified by MDAP (acidic conditions), to give the title compound (45 mg). LCMS (A) m/z: 541 [M+1]+, Rt 1.26 min (acidic).

Provenance & Evidence