Hydrochloric Acid → HCID 178481757, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.37 g, 7.59 mmol) and methylhydrazine (0.59 mL, 11.4 mmol) in n-BuOH (7 mL) was heated to 95° C. After 15 min, aqueous 38% HCl (0.55 mL, 8.83 mmol) was added and the mixture was heated to 120° C. After 4 h, water (10 mL) was added to the mixture and extracted with EtOAc (20 mL). The aqueous layer was separated and basified with saturated aqueous NaHCO3 to pH of 8 and extracted with EtOAc (2×20 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified via flash chromatography with a gradient of 5 to 60% EtOAc/heptane to give 1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.960 g, 73%): LC/MS (Table 2, Method b) Rt=1.49 min; MS m/z 173 (M+H)+.

Provenance & Evidence