Cesium carbonate → 2-methyl-1-(3-methylbutyl)-4-phenyl-7-{[1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl]amino}-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 7-chloro-2-methyl-1-(3-methylbutyl)-4-phenyl-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-one (25.00 mg, 0.073 mmol) and 5-amino-1-(tetrahydropyranyl)-1H-indazole (23 mg, 0.11 mmol) in toluene (2.00 mL) was added bis(dibenzylideneacetone)palladium (10.0 mg, 0.011 mmol), 2,2′-Bis-diphenylphosphanyl-[1,1′]binaphthalenyl (13.5 mg, 0.022 mmol) and Cs2CO3 (71 mg, 0.22 mmol). The resulting mixture was heated at 95° C. for 5 h. LC-MS indicated completion of reaction. The bulk of solvent was removed under reduced pressure to give a crude residue, which was purified by flash column chromatography on silica gel (eluent: 2% methanol in dichloromethane) to give the desired product: (Yield: 65%) MS(ES+): m/z 525.21 [MH+]. HPLC: tR=3.26 (ZQ3, Polar_5 min).

Provenance & Evidence