Water → 3-(4-fluoro-phenyl)-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[C:9]([CH:18]=[O:19])[NH:8][C:7]=1[CH2:20][CH2:21][NH2:22])=O)C.O.[OH-].[Li+].O>C(O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:6]3[C:4](=[O:3])[NH:22][CH2:21][CH2:20][C:7]=3[NH:8][C:9]=2[CH:18]=[O:19])=[CH:12][CH:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- temperatureto reflux under an argon atmosphere for 3 hours
- extractionextracted with a 5 to 1 solvent mixture of dichloromethane and methanol (50 ml×7)
- washwashed with brine
- dry with materialdried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude product was recrystallized from dichloromethane and methanol
Sources & evidence
- ORD record
- ord-a6b62233d4944688ac1b90de5562950d
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012966B2
Reaction notes
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