m-Chloroperbenzoic acid → HCID 86689852, compound

HRID 2409038Notes

Reaction equation

HRID 2409038 reaction equation
[F: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.C1C=C(Cl)C=C(C(OO)=[O:29])C=1>C(Cl)Cl>[F: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 86689853HCID 86689853, compound

Product 1

HCID 86689852HCID 86689852, compoundYield 121.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine (18 g, 62 mmol) in DCM (300 mL) was added MCPBA (16 g, 93 mmol). The mixture was stirred at RT overnight and then concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with DCM:MeOH (30:1) to afford 23 g (100%) of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine 4-oxide as a solid. MS (ESI) m/z: 307.1 [M+1]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by SiO2 chromatography
  3. washeluting with DCM:MeOH (30:1)

Sources & evidence

ORD record
ord-7b180a80aea04a798f9e9142c8739ba5
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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