Sodium t-butoxide → HCID 178481730, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-4-(cyclohexyl(2-methylhydrazono)methyl)-1H-pyrrolo[2,3-b]pyridine (0.241 g, 0.829 mmol), sodium tert-butoxide (0.191 g, 1.99 mmol), palladium acetate (0.001 g, 0.0083 mmol) and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-tert-butyl phosphine (0.0046 g, 0.0083 mmol), was heated in NMP (3 mL) at about 160° C. for about 15 min in a Biotage microwave. Additional palladium acetate (0.001 g, 0.0083 mmol) and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-tert-butyl phosphine (0.0046 g, 0.0083 mmol) was added and the reaction mixture was heated at about 160° C. for about 30 min. The insoluble residue was removed by filtration through a Celite® pad and to the filtrate was purified by preparative RP-HPLC (Table 2, Method r) to provide 1-cyclohexyl-3-methyl-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine as a white solid (0.121 g, 58%): LC/MS (Table 2, Method d) Rt=2.29 min; m/z: 255 (M+H)+.

Provenance & Evidence