3-Chlorobenzoic Acid → HCID 178526236, compound

HRID 340446Notes

Reaction equation

HRID 340446 reaction equation
ClC1C=C(C=CC=1)C(O)=[O:6].[Br:11][C:12]1[CH:20]=[CH:19][N:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2>C(Cl)(Cl)Cl>[Br:11][C:12]1[CH:20]=[CH:19][N+:18]([O-:6])=[C:17]2[NH:16][CH:15]=[CH:14][C:13]=12

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178526236HCID 178526236, compoundYield 132%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

m-Chlorobenzoic acid (1.0 g) was added to a chloroform (19 ml) solution containing 4-bromo-7-azaindole (760 mg) under ice cooling, followed by stirring for 30 minutes. Then, chloroform (10 ml) was distilled away under reduced pressure, diisopropylether was added, an insoluble precipitate was collected by filtration, and a white solid of 4-bromo-1H-pyrrolo[2,3-b]pyridine 7-oxide (1.085 g) was thus obtained.

Workup

  1. distillationThen, chloroform (10 ml) was distilled away under reduced pressure, diisopropylether
  2. additionwas added
  3. filtrationan insoluble precipitate was collected by filtration

Sources & evidence

ORD record
ord-5672040195f84237b371a92b504e4048
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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