Boron tribromide → 4-((6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)phenol

HRID 2176535Notes

Reaction equation

HRID 2176535 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]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57691265HCID 57691265, compound

Product 1

HCID 249016984-((6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

Workup

  1. customThe reaction was quenched with ice chips
  2. stirringstirred overnight at room temperature
  3. additionThe reaction mixture was diluted with dichloromethane
  4. custommethanol to give a clear mixture
  5. washthen washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe sample was purified by preparative TLC
  9. washeluting with 7% methanol in dichloromethane which

Sources & evidence

ORD record
ord-751b2ce2449d47dbb702d80687c67141
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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