m-Chloroperbenzoic acid → HCID 89925444, compound

HRID 922473Notes

Reaction equation

HRID 922473 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11]=[CH:10][C:9]=2[C:8]([CH3:20])=[CH:7]1.ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N+:11]([O-:26])=[CH:10][C:9]=2[C:8]([CH3:20])=[CH:7]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 89925439HCID 89925439, compound

Product 1

HCID 89925444HCID 89925444, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 1-(3-methoxypropyl)-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (100 mg) in chloroform (2 mL) was added meta-chloroperoxybenzoic acid (250 mg) under ice-cooling, and then the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and then the resulting residue was purified by NH-silica get column chromatography (eluent: ethyl acetate→ethyl acetate/methanol=10/1) to give ethyl 1-(3-methoxypropyl)-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate 5-oxide [REx(105-5)] (40 mg) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. customthe resulting residue was purified by NH-silica
  4. customget column chromatography (eluent: ethyl acetate→ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-f1905bf54bed4df39f844c4e316418dd
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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