m-Chloroperbenzoic acid → HCID 86689846, compound

HRID 2409031Notes

Reaction equation

HRID 2409031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:8][C:5]2=[N+:6]([O-:29])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86689845HCID 86689845, compound

Product 1

HCID 86689846HCID 86689846, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine (8.5 g, 27.7 mmol) in CH2Cl2 (150 mL) in an ice bath was added m-chloroperbenzoic acid (85%, 8.4 g, 41.6 mmol). The mixture was stirred at RT for two h. The reaction mixture was quenched by saturated sodium thiosulphate solution. The organic layer was washed with saturated NaHCO3 solution and water, dried (Na2SO4) filtered, and concentrated under reduced pressure to afford 8.75 g (90%) of 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-4-oxide as a yellow solid. MS (ESI): m/z=323.0 [M+1]+.

Workup

  1. customThe reaction mixture was quenched by saturated sodium thiosulphate solution
  2. washThe organic layer was washed with saturated NaHCO3 solution and water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1bf975ec82f4b599bac37524b31d091
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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