Potassium Carbonate → N-[6-Methyl-3-[3-(methyloxy)phenyl]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]cyclopropanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}cyclopropanesulfonamide (Example 95) (58 mg, 0.128 mmol), K2CO3 (57 mg, 0.412 mmol) and 1H-pyrazol-4-ylboronic acid (30 mg, 0.268 mmol) in 1,4-dioxane (1 mL) and water (0.4 mL), was added tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol). The reaction mixture was heated at 130° C. in a microwave reactor for 1 h and was then directly loaded onto a silica column, eluting with a gradient of 0-75% of ethyl acetate in cyclohexane and further purified by MDAP (acidic then basic conditions) to give the desired product and a white solid thought to be a salt of the desired product. The solid material was subsequently dissolved in DCM (1 mL) and treated with acetic acid (ca. 0.5 mL). The solvent was then removed to give a residue which was combined with the initially obtained product and the mixture further purified on silica, eluting with a gradient of 0-75% ethyl acetate in cyclohexane, to give the title compound (18 mg). LCMS (A) m/z: 441 [M+1]+, Rt 1.08 min (acidic).

Provenance & Evidence