N,N-dimethyl-3-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)propan-1-amine → N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(1-(3-(dimethylamino)propyl)-6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (300 mg, 0.7 mmol) and N,N-dimethyl-3-(6-methyl-3-(tributylstannyl)-1H-indazol-1-yl)propan-1-amine (1.4 g, 2.76 mmol) with tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.087 mmol), copper iodide (10 mg, 0.52 mmol) in 15 mL of dry DMF was heated to 85° C. overnight under N2. The reaction mixture was cooled to room temperature, diluted with 50 mL of water and the formed solid was separated by filtration. The solid was washed with 2-methoxy-2-methylpropane (5 mL) to give N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(1-(3-(dimethylamino)propyl)-6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (1 g, crude) which was used in the next step directly without further purification. LCMS: (M+H)+=564.

Provenance & Evidence