HCID 4777860, compound → HCID 68826346, compound

HRID 230564Notes

Reaction equation

HRID 230564 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([NH2:14])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.[Br-:15].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1>[Br:15][C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:9][C:8]=1[C:12]([NH2:14])=[O:13]

Participants

4

Reactant 2

HCID 4777860HCID 4777860, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 68826346HCID 68826346, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 540 mg (2.84 mmol) of 6-methoxy-1H-indole-2-carboxamide in 8 ml of pyridine is cooled to 0° C. and a solution of 908 mg (2.84 mmol) of pyridinium tribromide in 6 ml of pyridine is added thereto, dropwise. The reaction medium is stirred at 0° C. for 30 minutes and at ambient temperature for 19 h. 20 ml of ice-cold water is added to the reaction medium. The latter is then stirred at ambient temperature for 1 h and then filtered over sintered glass, to give 538 mg of 3-bromo-6-methoxy-1H-indole-2-carboxamide in the form of a white solid.

Workup

  1. stirringThe latter is then stirred at ambient temperature for 1 h
  2. filtrationfiltered over sintered glass

Sources & evidence

ORD record
ord-307d39c5ac5d4a5da56f39927f91dec5
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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