N-Methyl dicyclohexylamine → HCID 86723418, compound

Participants

Reaction Conditions

Reaction Steps

1,3-Dimethyl-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (Intermediate I) (180 mg, 0.586 mmol), 1-bromo-2,3-difluorobenzene (commercially available) (0.085 mL, 0.761 mmol) and N-cyclohexyl-N-methylcyclohexanamine (commercially available) (0.251 mL, 1.171 mmol) were combined in DMA (2.5 mL) and the mixture sparged with nitrogen for 30 min. [1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (commercially available) (38.2 mg, 0.059 mmol) was then added and the mixture heated at 110° C. for 1 hour under microwave irradiation. After cooling to room temperature, the mixture was heated at 110° C. for a further 6 hours. Further portions of 1-bromo-2,3-difluorobenzene (0.085 mL, 0.761 mmol) and [1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (38.2 mg, 0.059 mmol) were added, and the mixture heated at 110° C. for a further 5 h. Further [1,1′-Bis(di-tert-butylphosphino) ferrocene]dichloropalladium(II) (38.2 mg, 0.059 mmol) and 1-bromo-2,3-difluorobenzene (0.085 mL, 0.761 mmol) were added and the mixture heated 110° C. for a further 6 hours. Further [1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (38.2 mg, 0.059 mmol) was added and the mixture heated at 110° C. for a further 6 h. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic phase was dried over sodium sulphate and evaporated under reduced pressure. Purification by chromatography on silica, eluting with 15% EtOAc in iso-hexane afforded the title compound, which was used without further purification.

Provenance & Evidence