Sodium ethoxide → 3-amino-6-bromo-4-fluoro-1H-indole-2-carboxylic acid amide
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
Product 1
Reagents, catalysts & solvents 1
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]+