Phenacyl bromide → HCID 19916784, compound

HRID 1756058Notes

Reaction equation

HRID 1756058 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[CH2:11][C:12]#[N:13].[CH2:14](Br)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>C(#N)C>[Cl:1][C:2]1[N:10]=[C:5]2[N:6]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH2:11][C:12]#[N:13]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 193925832-Chloro-1H-pyrrolo[2,3-b]pyridine-3-acetonitrile

Product 1

HCID 19916784HCID 19916784, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0,66 g (3,4 mmol) 2-chloro-3-cyanomethyl-pyrrolo[2,3-b]pyridine, and 0,65 g (3,8 mmol) phenacyl bromide in 40 ml acetonitrile was refluxed for 20 h. The mixture was allowed to cool and the precipitated product was filtred off and recrystallized from acetonitrile. Chromatography on silica gel eluting with ethyl acetate gave the desired product (0,094g, 9%).

Workup

  1. temperatureto cool
  2. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-80880bdeb4384ee38347ed3109c47fb4
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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