Pyridiniumtribromide → 3-bromo-7-nitro-1H-indole-2-carboxamide

HRID 230566Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH2:15])=[O:14])=[CH:9]2)([O-:3])=[O:2].[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1>[Br:16][C:9]1[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[NH:11][C:10]=1[C:13]([NH2:15])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 2.57 g (12.53 mmol) of 7-nitro-1H-indole-2-carboxamide in 35 ml of pyridine is cooled to 0° C. in a water/ice bath. A solution of 4.01 g (12.53 mmol) of pyridinium tribromide in 20 ml of pyridine is then added at 0° C. dropwise, and the reaction is then stirred at 0° C. for 30 minutes and at ambient temperature for 16 h. 70 ml of ice-cold water are then added to the reaction medium. The latter is then stirred at ambient temperature for 15 minutes and is then filtered over sintered glass, to give 2.81 g of 3-bromo-7-nitro-1H-indole-2-carboxamide in the form of a brown solid.

Workup

stirringThe latter is then stirred at ambient temperature for 15 minutes
filtrationis then filtered over sintered glass

Sources & evidence

ORD record: ord-3027dac31ac64d04b08c638b60c63e7a
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566736B2

Reaction notes

Loading…