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

HRID 386060

Reaction equation

HRID 386060 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:9]=[N:10][N:11]([CH2:13][Si](C)(C)C)[CH:12]=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]([C:8]2[N:9]=[N:10][N:11]([CH3:13])[CH:12]=2)[N:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595259012-Bromo-6-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}pyridine

Product 1

HCID 595259902-Bromo-6-(1-methyl-1H-1,2,3-triazol-4-yl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-6-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}pyridine (550 mg, 1.77 mmol) in THF (10 mL) was added TBAF (1.0 M in THF, 5.30 mL, 5.30 mmol). The reaction was stirred at room temperature for 2 h. It was subsequently diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (20-100% EtOAc/hexanes) afforded 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-a28c191392de43429080cd5920469b5c
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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