Bromine → 6-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine
Reaction equation
[Br:1]Br.[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=1>CC(O)=O>[NH2:3][C@@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][NH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]([Br:1])=[CH:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of bromine (1.6 gm, 10 mmole) and HOAc (10 mL) was added in three portions to a stirred solution of 6-((S)-2-Amino-3-phenylpropylamino)-2-(4-pyridyl)pyridine (3.04 gm, 10 mmole) in HOAc (20 mL) at rt. After 1 hr, the mixture was concentrated and purified (SiO2, CH2Cl2/MeOH/NH4OH: 100/11/8) to give 6-((S)-2-Amino-3-phenylpropylamino)-3-bromo-2-(4-pyridyl)pyridine. MS (m/z): Calcd. C19H19N4Br (M+): 383, found : 383.1 and 385.1.