Diisopropylethylamine → HCID 178419831, compound

Participants

Reaction Steps

A solution containing 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.100 g, 0.554 mmol, Adesis), cyclohexylhydrazine hydrochloride (0.125 g, 0.831 mmol) and DIEA (0.19 mL, 1.1 mmol) in t-BuOH (5 mL) was stirred at ambient temperature for about 1 h, then heated at about 70° C. for about 1 h, followed by heating in a Biotage microwave at about 200° C. for about 1 h. The insoluble residue was removed by filtration and the filtrate was subjected to purification by preparative RP-HPLC (Table 2, Method p) to yield 1-cyclohexyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.045 g, 0.187 mmol, 34%) as an off-white solid: LC/MS (Table 2, Method d,) Rt 2.13 min; m/z: 241 (M+H)+, 239 (M−H)−.

Provenance & Evidence