Sodium ethoxide → 3-amino-6-bromo-4-fluoro-1H-indole-2-carboxylic acid amide

HRID 1182828Notes

Reaction equation

HRID 1182828 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:15])[C:5]([C:13]#[N:14])=[C:6]([NH:8][CH2:9][C:10]([NH2:12])=[O:11])[CH:7]=1.CC[O-].[Na+]>CC(O)C>[NH2:14][C:13]1[C:5]2[C:6](=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:15])[NH:8][C:9]=1[C:10]([NH2:12])=[O:11]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 581184952-(5-Bromo-2-cyano-3-fluorophenylamino)acetamide

Product 1

HCID 581185403-amino-6-bromo-4-fluoro-1H-indole-2-carboxylic acid amideYield 89%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

17.3 g (63.6 mmol) 2-(5-bromo-2-cyano-3-fluorophenylamino)acetamide was suspended in 150 ml 2-propanol and, after the addition of 10 ml NaOEt solution (21% in EtOH), the suspension was refluxed for 14 h. Having cooled down to room temperature, the solvent was concentrated and water was added. The resulting precipitate was sucked off and washed with water. 15.4 g (89%) 3-amino-6-bromo-4-fluoro-1H-indole-2-carboxylic acid amide was obtained. ESI-MS [m/z]: 272, 274 [M+H]+

Workup

  1. temperaturethe suspension was refluxed for 14 h
  2. concentrationthe solvent was concentrated
  3. additionwater was added
  4. washwashed with water

Sources & evidence

ORD record
ord-fe1d13a228ea46db9b291b37477cd410
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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