Benzophenone imine → HCID 87170790, compound

Participants

Reaction Conditions

Reaction Steps

Toluene (10 mL) was added to a mixture of rac-4-(3-bromo-phenyl)-4-methyl-4,7-dihydro-pyrazolo[1,5-a]pyrazin-6-ylamine (0.39 g, 1.28 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.12 g, 0.13 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.24 g, 0.38 mmol) and sodium tert-butoxide (0.22 g, 2.3 mmol) in a sealed tube and under nitrogen at room temperature. The mixture was flushed with nitrogen for a few minutes and then benzophenone imine (0.43 mL, 2.56 mmol) was added and the mixture was stirred at 100° C. for 2 hours. After cooling the mixture was diluted with water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in methanol in DCM 0/100 to 3/97). The desired fractions were collected and concentrated in vacuo to yield rac-4-[3-(benzhydrylidene-amino)-phenyl]-4-methyl-4,7-dihydro-pyrazolo[1,5-a]pyrazin-6-ylamine (0.37 g, 70% yield) as a yellow foam.

Provenance & Evidence