Sodium t-butoxide → HCID 178420309, compound

Participants

Reaction Steps

A mixture of 4-((1-benzylpiperidin-4-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine (0.85 g, 2.44 mmol), sodium tert-butoxide (0.565 g, 5.87 mmol), palladium acetate (0.0055 g, 0.024 mmol) and (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butyl phosphine (0.0136 g, 0.0244 mmol) was heated in NMP (10 mL) at about 160° C. in a CEM Discover microwave for about 30 min. The NMP was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL). The organic phase was separated, washed with brine (55 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was suspended in MeCN (10 mL) and the precipitate was collected by filtration and dried in vacuo to yield 1-(1-benzylpiperidin-4-yl)-3,6-dihydropyrazolo[4,3-d]pyrrolo[2,3-b]pyridine as a tan solid (0.33 g, 40%): LC/MS (Table 2, Method n) Rt=1.42 min; MS m/z: 332 (M+H)+.

Provenance & Evidence