Potassium Carbonate → Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

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Reaction Conditions

Reaction Steps

Alternatively, a mixture of ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 72) (8 g, 16.33 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (9.61 g, 32.7 mmol), tetrakis(triphenylphosphine)palladium(0) (0.944 g, 0.817 mmol) and potassium carbonate (6.77 g, 49.0 mmol) in 1,4-dioxane (50 mL), DMF (25 mL) and water (12.5 mL) was heated at 100° C. for ca. 3 h. After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate in DCM. The resulting material was then passed through an SCX cartridge, eluting with MeOH (ca. 200 mL) followed by 2M NH3 in MeOH (250 mL) and the basic methanolic fractions concentrated, to give the title compound (7.24 g). Some mixed fractions were further purified by MDAP (acidic conditions), to give the title compound (33 mg).

Provenance & Evidence