Potassium Carbonate → 3-chloro-N-[3-[3-(dimethylamino)phenyl]-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[3-bromo-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide (Example 100) (100 mg, 0.207 mmol), 3-(N,N-dimethylamino)-phenylboronic acid (68.2 mg, 0.413 mmol) and tetrakis(triphenylphosphine)palladium(0) (11.9 mg, 10.34 μmol) and potassium carbonate (86 mg, 0.620 mmol) in 1,4-dioxane (1 mL), DMF (0.5 mL) and water (0.25 mL) was heated at 110° C. overnight (ca. 22 h). After cooling to RT, the reaction mixture was filtered through celite and the filtrate concentrated and purified by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate in DCM. The material was then passed through an SCX cartridge, eluting with MeOH (ca. 60 mL) and 2M NH3 in MeOH (60 mL), to give the title compound (8 mg). LCMS (A) m/z: 524 [M+1]+, Rt 1.28 min (acidic).

Provenance & Evidence