m-Chloroperbenzoic acid → HCID 86720634, compound

HRID 2201814Notes

Reaction equation

HRID 2201814 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:26].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[C:6]2[CH:7]=[N+:8]([O-:26])[CH:9]=[CH:10][C:5]=2[N:4]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86720633HCID 86720633, compound

Product 1

HCID 86720634HCID 86720634, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of benzyl 3-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.4 g, 8.37 mmol) in dichloromethane (20 mL) was treated portion wise with 3-chloroperoxybenzoic acid (2.165 g, 12.55 mmol) followed by stirring at room temperature for about 1.5 hours. The reaction was neutralized with saturated aq. sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to afford benzyl 3-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxide (2.45 g, 99%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a82af03e02574339a9a1e0eef32d8a8e
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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