m-Chloroperbenzoic acid → HCID 178526240, compound

HRID 452628Notes

Reaction equation

HRID 452628 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>C(#N)C>[C:1]1([CH2:7][CH2:8][C:9]2[NH:17][C:12]3=[N+:13]([O-:26])[CH:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68663939HCID 68663939, compound

Product 1

HCID 178526240HCID 178526240, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine (1.97 g, 8.86 mmol) in acetonitrile (100 mL) was added m-chloroperbenzoic acid (2.82 g, 10.63 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 20 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) to give the title compound (1.17 g, yield 55%) as a yellow amorphous form.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)

Sources & evidence

ORD record
ord-190b4ab7ab954294a0a2d4825a4ec7c5
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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