Hydrogen Peroxide → 4-Bromo-1H-indole-6-carboxamide

HRID 2365165Notes

Reaction equation

HRID 2365165 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH:13]O.[OH-].[Na+].O>CO>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([NH2:12])=[O:13])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 247288834-bromo-1H-indole-6-carbonitrile

Product 1

HCID 668705554-Bromo-1H-indole-6-carboxamideYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-bromo-1H-indole-6-carbonitrile (1 g, 4.50 mmol) in methanol (10 mL) was treated with 30% aqueous hydrogen peroxide (2.7 mL, 4.95 mmol) and a 1 M aqueous sodium hydroxide solution (5 mL) then heated at 40° C. for 1 h. The reaction mixture was cooled, treated with water and cooled in an ice-bath. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to obtain 4-bromo-1H-indole-6-carboxylic acid amide (1.05 g, 97%), which was transformed into the title boronic ester by the general method (Scheme 1) (0.80 g, 67%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperaturecooled in an ice-bath
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5c2e0d2757b24f4fb0c9ce4d181c28b8
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

Loading…