Phenethyl bromide → HCID 19916808, compound

HRID 1756044Notes

Reaction equation

HRID 1756044 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13])#[N:2].Br[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[C:1]([CH2:3][C:4]1[C:12]2[C:7]([N:8]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=[CH:10][CH:11]=2)=[N:6][C:5]=1[CH3:13])#[N:2]

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 19916764(2-Methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetonitrile

Product 1

HCID 19916808HCID 19916808, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 130 mg (0.76 mmol) of 3-cyanomethyl-2-methyl-pyrrolo[2,3-b]pyridine and 150 mg (0.81 mmol) of 2-bromoethyl-benzene in 2 ml of acetonitrile was refluxed for 40 h. The solvent was evaporated and the crude product was chromatographed on silica gel with ethyl acetate: methanol: water 100:12:4. Recrystallization from a small amount of ether: petroleumether 1:1 gave 53 mg (25%) of 3-cyanomethyl-2-methyl-7-(2-phenylethyl)pyrrolo[2,3-b]pyridine.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was chromatographed on silica gel with ethyl acetate: methanol: water 100:12:4
  3. customRecrystallization from a small amount of ether

Sources & evidence

ORD record
ord-7088549b026240f89813c33ff2520d2f
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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