4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde → HCID 178420311, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.40 g, 2.21 mmol, Adesis) and 1-benzyl-3-hydrazinylpiperidine hydrochloride (1.39 g, 4.43 mmol) were suspended in n-BuOH (11.1 mL). The mixture was heated at about 90° C. for about 3 h and then heated at about 120° C. for about 5 h. The reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to yield 1-(1-benzylpiperidin-3-yl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.105 g, 14%) as a brown oil: LC/MS (Table 1, Method b) Rt=1.53 min; MS m/z: 332 (M+H)+.

Provenance & Evidence