Boron tribromide → 4-((6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)phenol
Reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][C:8]2[N:12]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=[CH:16][C:11]3=[N:10][N:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[C:17]1([C:14]2[CH:15]=[CH:16][C:11]3[N:12]([C:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:24][CH:23]=4)=[N:9][N:10]=3)[CH:13]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-(4-Methoxybenzyl)-6-phenyl-[1,2,4]triazolo[4,3-a]pyridine (0.057 g, 0.18 mmol) was dissolved in dichloromethane (2.5 mL) then cooled to 0° C. A 1M solution of boron tribromide (0.72 ml, 0.72 mmol) in dichloromethane was added slowly. The reaction mixture was stirred at 0° C. for 2 hours. A precipitate was present in the reaction mixture. The reaction was quenched with ice chips and stirred overnight at room temperature. A solid remained in the mixture. The reaction mixture was diluted with dichloromethane/methanol to give a clear mixture then washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The sample was purified by preparative TLC eluting with 7% methanol in dichloromethane which afforded 4-((6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)phenol as an off-white solid