Sodium Hydroxide → HCID 178462888, compound

Participants

Reaction Steps

To a solution of 2-(4-amino-1H-pyrazol-3-yl)-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (250 mg, 0.81 mmol), diisopropylethylamine (0.36 ml, 2.01 mmol) in THF (0.8 ml), 4-fluorobenzoyl chloride (114 μL, 0.97 mmol) was slowly added at rt. The mixture was stirred overnight at rt. Aqueous NaOH (2 mL, 1M) was added and the solvent was evaporated. Water (25 ml) was added and the mixture was extracted three times with ethyl acetate (3×25 ml). The combined organic layers were washed with brine, dried and evaporated to afford a residue which precipitated after addition of methanol. The precipitate was suspended in MeOH/CH3CN (1:1, 6 mL) and refluxed for 2 hours in aqueous KOH (0.50 mL, 5M). After evaporation of the solvent and addition of water, a white solid was isolated and dried under high vacuum. The title compound was obtained (77 mg).

Provenance & Evidence