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

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-(morpholino)phenylboronic acid, pinacol ester (99 mg, 0.343 mmol), tetrakis(triphenylphosphine)palladium(0) (19.79 mg, 0.017 mmol), bis(triphenylphosphine)palladium(II) chloride (12.02 mg, 0.017 mmol) and potassium carbonate (71.0 mg, 0.514 mmol) 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 120° C. for 15 min. At this point, the five reaction mixtures were combined and concentrated. The residue was passed through an SCX cartridge, eluting with MeOH (150 mL) and then 2M NH3 in MeOH (200 mL). The basic methanolic solution was concentrated and the residue was purified by MDAP (acidic conditions), to give the title compound (115 mg).

Provenance & Evidence