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

HRID 892872Notes

Reaction equation

HRID 892872 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]=1

Participants

4

Reactant 2

HCID 149943831H-Pyrrolo[2,3-b]pyridine-5-methanol, 4-(4-fluorophenyl)-6-(1-methylethyl)-HCID 178418287HCID 178418287, compound

Product 1

HCID 149943844-(4-Fluorophenyl)-6-isopropyl-1H-pyrrolo[2,3-B]pyridine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. additionare added
  2. filtrationThe suspension is filtered through 1.2 kg of silica gel (230-400 mesh) in a glass suction
  3. filtrationfilter
  4. washwashed
  5. customwithout sucking dry
  6. concentrationThe eluate is concentrated to dryness in vacuo
  7. stirringthe residue which remains is stirred thoroughly in ether

Sources & evidence

ORD record
ord-fd7bd6ca0f0949d0abae8ae6a2078d0c
Source dataset
uspto-grants-1992_06
Patent number
US05120782

Reaction notes

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