Potassium Carbonate → 3-Chloro-N-[3-[5-(dimethylamino)-3-pyridinyl]-6-methyl-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) (150 mg, 0.257 mmol), dimethylamino pyridine boronic acid (85 mg, 0.514 mmol), potassium carbonate (107 mg, 0.771 mmol), tetrakis(triphenylphosphine)palladium(0) (7.42 mg, 6.42 μmol) and bis(triphenylphosphine)palladium(II) chloride (4.51 mg, 6.42 μmol) were weighed into a microwave vial. 1,4-Dioxane (2.0 mL), DMF (1.0 mL) and water (0.5 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 (100 mL) and then with 2M NH3 in MeOH (150 mL). The basic methanolic solution was concentrated and purified by MDAP (acidic conditions) and then further purified by normal phase chromatography, eluting with a gradient of 0-10% MeOH in DCM, to give the title compound (63 mg). LCMS (A) m/z: 523 [M−1]−, Rt 0.78 min (acidic).

Provenance & Evidence