Bromine → 3,7-dibromo-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one
Reaction equation
N1C2C=CC=CC=2CCCC1.[Br:12]Br.[Br:14][CH:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[NH:17][C:16]1=[O:26]>C(O)(=O)C>[Br:14][CH:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[C:23]([Br:12])[CH:24]=[CH:25][C:18]=2[NH:17][C:16]1=[O:26]Participants
5
Procedure
Scheme 5 describes an example of bromination of a tetrahydrobenzazepine intermediate. Bromine can be added slowly to commercially available 3-bromo-1,3,4,5-tetrahydro-1-benzazepin-2-one in acetic acid with stirring at room temperature to provide the useful intermediate 3,7-dibromo-1,3,4,5-tetrahydro-1-benzazepin-2-one, which can be used in many transformations described herein. Bromination using similar conditions can be carried out on other amino aryl cores described herein to provide intermediates for transformation to the compounds of the invention described in Schemes 8, 9 and 10.