Bromine → 3-Bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one
Reaction equation
[Br:1]Br.[N:3]1[C:8]2[NH:9][C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(Cl)Cl>[Br:1][C:5]1[CH:4]=[N:3][C:8]2[NH:9][C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:7]=2[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 10% solution of bromine (0.57 mL, 11.1 mmole) in CH2Cl2 was added dropwise over 1 hr to a solution of 5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one (1.20 g, 7.4 mmole) in CH2Cl2 at RT. The mixture was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 10% Na2CO3 and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (EtOAc) gave the title compound (1.00 g, 56%) as a light yellow solid after drying in vacuo: MS (ES) m/e 241/243.