反应详情

A stirred solution of 2-(2-amino-ethyl)-4-(4-fluoro-phenyl)-5-formyl-1H-pyrrole-3-carboxylic acid ethyl ester (257.5 mg, 2.5 mmol), lithium hydroxide monohydrate (840 mg, 20 mmol) in ethanol (95%, 20 ml) was heated to reflux under an argon atmosphere for 3 hours. The mixture was added with cold water (150 ml), stirred for 10 minutes, extracted with a 5 to 1 solvent mixture of dichloromethane and methanol (50 ml×7), washed with brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was recrystallized from dichloromethane and methanol to give 3-(4-fluoro-phenyl)-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde (170 mg, 26.3%) as a red solid.

1. temperatureto reflux under an argon atmosphere for 3 hours
2. extractionextracted with a 5 to 1 solvent mixture of dichloromethane and methanol (50 ml×7)
3. washwashed with brine
4. dry with materialdried with anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe crude product was recrystallized from dichloromethane and methanol