5-fluoro-4-(trimethylstannyl)-1H-indole → 2-(5-Fluoro-1H-indol-4-yl)-4-morpholin-4-yl-6-piperazin-1-ylmethyl-thieno[3,2-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-fluoro-4-(trimethylstannyl)-1H-indole (100 mg, 0.33 mmol), 4-(2-methylsulfanyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (71 mg, 0.15 mmol) and copper(I) bromide-dimethyl sulfide complex (70 mg, 0.33 mmol) in THF (3 mL) was degassed with argon, treated with tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.008 mmol) and heated at 90° C. overnight. The reaction mixture was purified by column chromatography. The foregoing compound was treated with TFA-DCM (1:1, 2 mL), evaporated in vacuo and purified by ion-exchange chromatography (Isolute® SCX-2 cartridge, eluting with NH3 in methanol) and preparative TLC to give the title compound (6.5 mg, 10%).

Provenance & Evidence