m-Chloroperbenzoic acid → 6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine 4-oxide
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.