m-Chloroperbenzoic acid → HCID 10595309, compound

HRID 1872050Notes

Reaction equation

HRID 1872050 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[N:18]=2)[C:13]([C:21]#[N:22])=[CH:12]1.ClC1C=C(C=CC=1)C(OO)=[O:28].ClCCl.CO>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[N:18]=2)[C:13]([C:21]#[N:22])=[CH:12]1.[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[N+:18]=2[O-:28])[C:13]([C:21]#[N:22])=[CH:12]1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 10641825HCID 10641825, compoundHCID 21226129Dichloromethane methanol

Product 2

HCID 10595309HCID 10595309, compoundYield 142%HCID 10641825HCID 10641825, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Part A: A solution of 1.24 g of 1-(2-bromo-4-isopropyl-phenyl)-3-cyano-6-methyl-7-azaindole (Example 72) and 1.42 g of 85% of 3-chloroperoxybenzoic acid in 20 mL of chloroform was refluxed for 6 hrs. The mixture was cooled and washed first with 10% sodium bicarbonate solution, then with brine. The solution was dried (Na2SO4) and evaporated to give a residue. TLC on silica gel with 95:5 dichloromethane-methanol showed a trace spot at Rf 0.88 and a major spot at Rf 0.34. The material was purified by chromatography on silica gel with dichloromethane, followed by 1% methanol in dichloromethane, to give a trace of unchanged 1-(2-bromo-4-isopropylphenyl)-3-cyano-6-methyl-7-azaindole Rf 0.88) and 0.92 g of 1-(2-bromo-4-isopropylphenyl)-3-cyano-6-methyl-7-azaindole-7-oxide (Rf 0.34); mp 179.2°, Mass spec. (m+H)+ =370.0559; calcd., 370.0555 (79Br).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed first with 10% sodium bicarbonate solution
  3. dry with materialThe solution was dried (Na2SO4)
  4. customevaporated
  5. customto give a residue
  6. customThe material was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-bcb56d3dd69f42e783c75d5de6cc8ad4
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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