5-Trimethylstannanyl-indazole-1-carboxylic acid tert-butyl ester → 5-{4-bromo-5-[((1R,2R)-2-methyl-cyclopropanecarbonyl)-amino]-isothiazol-3-yl}-indazole-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve (1R,2R)-2-methyl-cyclopropanecarboxylic acid (3,4-dibromo-isothiazol-5-yl)-amide (3.0; g, 8.82; mmol) in anhydrous 1,4-dioxane (88; mL) and add 5-trimethylstannanyl-indazole-1-carboxylic acid tert-butyl ester (4. 11; g, 9.70; mmol). Blanket under nitrogen, add bis(triphenylphosphine)palladium(II) chloride (0.62; g, 0.88 mmol) and heat to 85° C. for 4; days. Concentrate and purify the residue by silica gel chromatography, gradient eluting from 20:80; to 40:60; ethyl acetate:hexanes to give the title compound (1.04; g, 70% purity wt/wt, 17%) which is carried on with out further purification. MS (m/z): 477, 479; (M+1).

Provenance & Evidence