1H-Pyrrolo[2,3-b]pyridine-5-methanol, 4-(4-fluorophenyl)-6-(1-methylethyl)- → 4-(4-Fluorophenyl)-6-isopropyl-1H-pyrrolo[2,3-B]pyridine-5-carbaldehyde
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[C:10]3[NH:19][CH:20]=[CH:21][C:9]=23)=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[O:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[C:10]3[NH:19][CH:20]=[CH:21][C:9]=23)=[CH:4][CH:3]=1Participants
4
Procedure
23.9 g (84 mmol) of the compound from Example VII are suspended in 1.6 1 of dichloromethane, 17.1 g of neutral alumina and 36.1 g (168 mmol) of pyridinium chlorochromate are added and the mixture is stirred at room temperature for 1 h. The suspension is filtered through 1.2 kg of silica gel (230-400 mesh) in a glass suction filter and washed without sucking dry using petroleum ether/ethyl acetate 3:2. The eluate is concentrated to dryness in vacuo and the residue which remains is stirred thoroughly in ether.