Acetyl chloride → 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

HRID 2382080Notes

Reaction equation

HRID 2382080 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[C:14](Cl)(=[O:16])[CH3:15]>C(Cl)Cl>[NH:1]1[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[C:4]2[C:3]([C:14](=[O:16])[CH3:15])=[CH:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 127782161-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethan-1-oneYield 23.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Ref.: J. Org. Chem. 2002, 67, 6226-6227) 7-Azaindole (5 g, 42.3 mmol) is added to a stirred suspension of AlCl3 (22.6 g, 169 mmol) in DCM (300 mL). After stirring at rt for 1 h, acetyl chloride (13.3 g, 169 mmol) is added drop wise and the resulting mixture is stirred for 18 h. The mixture is cooled to 00 C., quenched with MeOH (150 mL) and stirred for 1 h. Silica gel is added to the mixture, the solvents are removed under vacuum, and the residue is purified by silica gel chromatography eluting with 10% MeOH in DCM to afford 1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (1.6 g). 1H NMR (300 MHz, CH3OD): δ 8.93(d, 1H), 8.45(s, 2H), 7.50(t, 1H), 3.30(s, 3H).

Workup

  1. stirringthe resulting mixture is stirred for 18 h
  2. temperatureThe mixture is cooled to 00 C
  3. custom, quenched with MeOH (150 mL)
  4. stirringstirred for 1 h
  5. additionSilica gel is added to the mixture
  6. customthe solvents are removed under vacuum
  7. customthe residue is purified by silica gel chromatography
  8. washeluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-3ab44006e72e4befb4a129c8e5c98382
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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