2-bromo-N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide → N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (1.73 g, 2.58 mmol), 6-methyl-3-(tributylstannyl)-1H-indazole (1.2 g, 2.84 mmol), Pd(PPh3)4 (298 mg, 0.258 mmol) and CuI (98 mg, 0.516 mmol) in dry DMF (20 mL) was heated to 90° C. for 4 hours. Product was extracted with ethyl acetate (200 mL), organic phase washed with water (2×50 mL) and brine (2×50 mL), then dried over Na2SO4, filtered and concentrated. The residue was triturated with petroleum ether (10 mL) then decanted and dried to afford N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (1.21 g, 65%) as a yellow solid. LCMS: (M+H)+=721.

Provenance & Evidence