Bromine → 4-(4-Methoxybenzylthio)-5-bromopyridin-2-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:5][CH:4]=1.[Br:18]Br>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[C:14]([Br:18])=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:16][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(4-methoxybenzylthio)pyridine-2-amine (2.4 g, 9.7 mmol) was dissolved in acetic acid (30 mL). Bromine (1M in AcOH, 9.8 ml, 9.8 mmol) was added dropwise at ambient temperature and the reaction stirred for 30-minutes. The solution was concentrated and the residue was neutralized with saturated NaHCO3 solution. The solution was extracted with EtOAc and the organic layer was dried and concentrated. The residue was purified by flash chromatography (70% EtOAc/hexanes) to obtain the desired product (1.71 g, 54% yield) as a yellow solid.