Tetrabutylammonium Fluoride → 2-Bromo-6-[fluoro(1-methyl-1H-1,2,3-triazol-4-yl)methyl]pyridine

HRID 386068Notes

Reaction equation

HRID 386068 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:19])[C:9]2[N:10]=[N:11][N:12]([CH2:14][Si](C)(C)C)[CH:13]=2)[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:19])[C:9]2[N:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[N:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595258952-Bromo-6-(fluoro{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)pyridine

Product 1

HCID 595262522-Bromo-6-[fluoro(1-methyl-1H-1,2,3-triazol-4-yl)methyl]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-6-(fluoro{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)pyridine (500 mg, 1.46 mmol) in THF (10 mL) was added TBAF (1.0 M in THF, 4.37 mL, 4.37 mmol). The reaction was stirred at room temperature for 2 h. It was then diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (30-100% EtOAc/hexanes) provided the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a02eca84896649d49b02846a3e4e6d6c
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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