1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole → methyl 2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-bromo-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (300 mg, 0.81 mmol) and 1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole (396 mg, 0.89 mmol) in DMF (10 mL) were added CuI (30 mg, 0.16 mmol) and Pd(PPh3)4 (47 mg, 0.041 mmol), the reaction mixture was degassed by bubbling nitrogen for 3 minutes and refilled with nitrogen. The mixture was heated to 80° C. for 5 hours under nitrogen, after cooling, water (50 mL) was added to the mixture and product extracted with EtOAc (3×40 mL), the combined organic layers were dried over Na2SO4, concentrated under reduced pressure and the residue was triturated with petroleum ether (2 mL) then decanted and dried to give methyl 2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (280 mg, 70.7%) as an orange solid. LCMS: (M+H)+=490.

Provenance & Evidence