Tetrabutylammonium Fluoride → 2-chloro-6-(1H-1,2,3-triazol-1-yl)pyridine

HRID 386056Notes

Reaction equation

HRID 386056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[C:11]([Si](C)(C)C)[N:10]=[N:9]2)[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)[N:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595262262-Chloro-6-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]pyridine

Product 1

HCID 212903442-chloro-6-(1H-1,2,3-triazol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-6-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]pyridine (675 mg, 2.67 mmol) in THF (10 mL) was added TBAF (1.0 M in THF, 8.01 mL, 8.01 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. The crude residue was purified by flash chromatography (10-60% EtOAc/hexanes) to afford 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
  6. customThe crude residue was purified by flash chromatography (10-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-48dd3ace1d97463f92636a0a185aacb3
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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