m-Chloroperbenzoic acid → 5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine 6-oxide

HRID 472022Notes

Reaction equation

HRID 472022 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[C:15]=1[C:22]1[CH:23]=[C:24]2[CH:30]=[CH:29][N:28]([CH:31]([CH2:35][CH2:36][CH3:37])[CH2:32][CH2:33][CH3:34])[C:25]2=[CH:26][N:27]=1)[CH3:13]>C(Cl)Cl>[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[C:15]=1[C:22]1[CH:23]=[C:24]2[CH:30]=[CH:29][N:28]([CH:31]([CH2:32][CH2:33][CH3:34])[CH2:35][CH2:36][CH3:37])[C:25]2=[CH:26][N+:27]=1[O-:9])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 116817955-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

Product 1

HCID 671525095-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine 6-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-benzenecarboperoxoic acid (c.a. 60%, 198 mg, 0.69 mmol) is added to a solution of 5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine (200 mg, 0.057 mmol) in DCM (4 mL), and the mixture is stirred for 30 min at room temperature. The mixture is washed with a saturated aqueous Na2CO3 solution, brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the residue on silica gel (EtOAc) gives 5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridine 6-oxide as a white solid.

Workup

  1. washThe mixture is washed with a saturated aqueous Na2CO3 solution, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89e6d90b0bbe4cd9b22167a23b8e2f2d
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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