2-Chloro-4'-fluoroacetophenone → 2-Chloro-3-methyl-7-(p-fluorophenacyl)pyrrolo [2,3-b]pyridine hydrochloride

HRID 1756056Notes

Reaction equation

HRID 1756056 reaction equation
[Cl:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].[F:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=[O:20])[CH2:18]Cl)=[CH:15][CH:14]=1>C(#N)C>[ClH:1].[Cl:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:18][C:17]([C:16]3[CH:21]=[CH:22][C:13]([F:12])=[CH:14][CH:15]=3)=[O:20])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 1202482-Chloro-4'-fluoroacetophenoneHCID 193925862-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 199167742-Chloro-3-methyl-7-(p-fluorophenacyl)pyrrolo [2,3-b]pyridine hydrochlorideYield 114.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,2 g (7,2 mmol) 2-chloro-3-methylpyrrolo[2,3-b]pyridine and 1,5 g (8,7 mmol) p-fluorophenacyl chloride in 50 ml acetonitrile was refluxed for 48 h. The mixture was allowed to cool and the precipitated product filtered off. The solid was treated with ethyl acetate and filtered off again affording 1,4 g (57%) of the desired product.

Workup

  1. temperatureto cool
  2. filtrationthe precipitated product filtered off
  3. additionThe solid was treated with ethyl acetate
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-5fa0e64f153748ecbc994eb300292936
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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