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

HRID 75269Notes

Reaction equation

HRID 75269 reaction equation
[Br: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>[Br: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 867079586-Bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 867079596-Bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine 4-oxideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine (6.87 g, 19.56 mmol) in DCM (100 mL) at 0° C. was added 3-chloroperbenzoic acid (77 wt %, 5.26 g, 23.47 mmol). The reaction mixture was stirred at RT until the starting material was completely consumed, as monitored by HPLC. After 8 h, the solution was washed with saturated aqueous NaHCO3 (2×). The organic phase was dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (2% to 4% MeOH/DCM) to give the title compound as a white solid (5.66 g, 79%). 1H NMR (500 MHz, CDCl3) δ ppm 8.30 (s, 1H), 8.06 (s, 1H), 7.78 (d, 2H, J=8.0 Hz), 7.65 (d, 1H, J=3.5 Hz), 7.33 (d, 2H, J=8.0 Hz), 7.06 (d, 1H, J=3.5 Hz), 2.41 (s, 3H); ESI-MS m/z [M+H]+ calc'd for C14H11BrN2O3S, 367, 369; found 367, 369.

Workup

  1. customwas completely consumed
  2. washthe solution was washed with saturated aqueous NaHCO3 (2×)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (2% to 4% MeOH/DCM)

Sources & evidence

ORD record
ord-66af31253d7c4d539a71a99cd7ce7e9e
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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