m-Chloroperbenzoic acid → HCID 178526236, compound

HRID 331012Notes

Reaction equation

HRID 331012 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:19])=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178526236HCID 178526236, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (2 g, 10.15 mmol) in diethyl ether (160 mL) was cooled to 0° C. mCPBA (3.64 g, 16.24 mmol) was added to the mixture at 0° C. After stirring for 20 min at this temperature, the mixture was allowed to warm to RT and stirred for 3 hours. The formed precipitate was filtered and washed with cold ether to give the title compound (1.978 g). LCMS (A): m/z (M+H)+ 213/215, C7H5BrN2O requires 212/214 (acidic).

Workup

  1. additionwas added to the mixture at 0° C
  2. stirringstirred for 3 hours
  3. filtrationThe formed precipitate was filtered
  4. washwashed with cold ether

Sources & evidence

ORD record
ord-e1a870b85c644444a04604cd02bccb9d
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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