m-Chloroperbenzoic acid → HCID 178526273, compound

HRID 506790Notes

Reaction equation

HRID 506790 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:19])C=1.ClCCl.CO>C(COC)OC>[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N+:6]([O-:19])[CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridineHCID 21226129Dichloromethane methanol

Product 1

HCID 178526273HCID 178526273, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5-Fluoro-1H-pyrrolo[2,3-b]pyridine 7-oxide can be obtained as in example 4 stage 4(a) but starting from 2.7 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine, and 6.22 g of 3-chloro-perbenzoic acid in 70 cm3 of dimethoxyethane. In this way, after flash chromatography on a silica column [eluent: dichloromethane/methanol (95/5 by volume)], 1.70 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine 7-oxide is obtained as a powder with the following characteristics:

Sources & evidence

ORD record
ord-e45435388ce64404aa1c0692f67b7721
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

Loading…