4-(Bromoacetyl)benzonitrile → 2,3Dimethyl-7-(p-cyanophenacyl)pyrrolo[2,3-b]pyridine

HRID 1756061Notes

Reaction equation

HRID 1756061 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].[C:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18](=[O:21])[CH2:19]Br)=[CH:16][CH:15]=1)#[N:13]>CC#N>[CH3:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:19][C:18]([C:17]3[CH:22]=[CH:23][C:14]([C:12]#[N:13])=[CH:15][CH:16]=3)=[O:21])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 125323872,3-Dimethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 193925742,3Dimethyl-7-(p-cyanophenacyl)pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,3-dimethylpyrrolo[2,3-b]pyridine (146 mg, 1 mmol) and p-cyanophenacyl bromide (248 mg, 1.1 mmol) in 3 ml CH3CN was refluxed for 1.5 h. The mixture was allowed to cool and the precipitated product filtered off and washed with a small volume of ice cold CCl4 affording 313 mg (85%) pure title compound as the hydrobromide salt.

Workup

  1. temperatureto cool
  2. filtrationthe precipitated product filtered off
  3. washwashed with a small volume of ice cold CCl4 affording 313 mg (85%) pure title compound as the hydrobromide salt

Sources & evidence

ORD record
ord-47dd8c6b521242d3b32ebcb6798e3b8a
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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