methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate → methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (500 mg, 0.72 mmol) in CH3OH (15 mL) was added Pd/C (0.1 g, cat.) and HCO2NH4 (226 mg, 3.6 mmol), after the addition, the reaction mixture was heated to 80° C. with stirring for 0.5 hour, then the mixture was filtered and filtrate evaporated, the residue was partitioned between H2O (25 mL) and EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL) dried over Na2SO4, filtered and concentrated under reduced pressure to give methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (400 mg, 85%) as yellow solid. LCMS: (M+H)+=665.

Provenance & Evidence