Phenacyl bromide → 5-Bromo-2,3-dimethyl-7-phenacyl pyrrolo[2,3-b]pyridine

HRID 1756075Notes

Reaction equation

HRID 1756075 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:5]2=[N:6][CH:7]=1.BrC1N=C2NC(C)=C(C)C2=CC=1.[CH2:25](Br)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]=[C:5]2[N:6]([CH2:25][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:27])[CH:7]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 193925846-Bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridineHCID 193926125-Bromo-2,3-dimethyl-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 193925755-Bromo-2,3-dimethyl-7-phenacyl pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-bromo-2,3 -dimethyl-pyrrolo [2,3 -b]pyridine (prepared in a similar manner as 6-bromo-2,3-dimethyl-pyrrolo[2,3-b]pyridine (200 mg, 0.9 mmol) and phenacyl bromide (200 mg, 1.3 mmol) in 15 ml CH3CN was refluxed for 16 h. The mixture was allowed to cool and the precipitated product filtered off and washed with a small volume of diethyl ether affording 243 mg (72%) pure title compound as the hydrochloride.

Workup

  1. temperaturewas refluxed for 16 h
  2. temperatureto cool
  3. filtrationthe precipitated product filtered off
  4. washwashed with a small volume of diethyl ether affording 243 mg (72%) pure title compound as the hydrochloride

Sources & evidence

ORD record
ord-fe6df80c6c8c452795d8770868e1bca0
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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