m-Chloroperbenzoic acid → 6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine 4-oxide

HRID 75273Notes

Reaction equation

HRID 75273 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]2[N:21]([CH3:22])[CH:20]=[CH:19][C:16]2=[N:17][CH:18]=1>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]2[N:21]([CH3:22])[CH:20]=[CH:19][C:16]2=[N+:17]([O-:9])[CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 673831026-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 867079626-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine 4-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (77 wt %, 3.46 g, 15.4 mmol) was added to a stirred solution of 6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine (2.96 g, 14.0 mmol) in DCM (60 mL) at 0° C. The reaction mixture was stirred at RT for 4 hours and then concentrated and purified by silica gel chromatography (7% MeOH/DCM) to give the title compound as a brown semi-solid, which was used without further purification (3.8 g). ESI-MS m/z [M+H]+ calc'd for C8H7BrN2O, 227, 229; found 227, 229.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (7% MeOH/DCM)

Sources & evidence

ORD record
ord-b1759c9f9d484b5a9f6c8482b0874ea6
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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