Acetyl chloride → 1-(1H-pyrrolo(2,3-c)pyridin-3-yl)ethanone

HRID 2382085Notes

Reaction equation

HRID 2382085 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH: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=[CH:8][N: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 92196-AzaindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 118297291-(1H-pyrrolo(2,3-c)pyridin-3-yl)ethanoneYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Ref.: J. Org. Chem. 2002, 67, 6226-6227) 6-Azaindole (2.5 g, 21.25 mmol) is added to a stirred suspension of AlCl3 (11.3 g, 84.5 mmol) in CH2Cl2 (150 mL). After stirring at rt for 1 h, acetyl chloride (6.65 g, 84.5 mmol) is added drop wise and the resulting mixture is stirred for 18 h. The mixture is cooled to 0° C., quenched with MeOH (75 mL) and stirred for 1 h. Silica gel (40 mL), MeOH and DCM are added to the mixture, the solvents are removed under vacuum and the residue is purified by silica gel chromatography eluting with 10% MeOHl in DCM to afford 1-(1H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (1.52 g, 45%). MS: 161 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.20 (s, 1H), 8.95 (s, H), 7.82(d, 1H), 8.72 (d, 1H), 8.43 (d, 1-H), 2.64(s, 3H).

Workup

  1. stirringthe resulting mixture is stirred for 18 h
  2. temperatureThe mixture is cooled to 0° C.
  3. customquenched with MeOH (75 mL)
  4. stirringstirred for 1 h
  5. additionSilica gel (40 mL), MeOH and DCM are added to the mixture
  6. customthe solvents are removed under vacuum
  7. customthe residue is purified by silica gel chromatography
  8. washeluting with 10% MeOHl in DCM

Sources & evidence

ORD record
ord-f3be463bc7e44929b8bc7cfa55ca1945
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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