Trimethylsilylmethyl Azide → 2-Bromo-6-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}pyridine

HRID 386059

Reaction equation

HRID 386059 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[N:3]=1.[CH3:10][Si:11]([CH2:14][N:15]=[N+:16]=[N-:17])([CH3:13])[CH3:12].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:17]=[N:16][N:15]([CH2:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[CH:9]=2)[N:3]=1

Participants

7

Reactant 3

HCID 150751Trimethylsilylmethyl AzideHCID 129705322-Bromo-6-ethynylpyridineHCID 23667548Sodium Ascorbate

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Bromo-6-ethynylpyridine (Example 465, Step 1) (350 mg, 1.92 mmol) and trimethylsilylmethyl azide (323 mg, 2.50 mmol) were combined in t-BuOH (4.0 mL) and water (3.0 mL). CuSO4.5H2O (24 mg, 0.096 mmol) in water (0.50 mL) was added, followed by sodium ascorbate (76 mg, 0.39 mmol) in water (0.50 mL). The reaction was stirred at room temperature overnight, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to a yellow residue that was purified by flash chromatography (0-50% 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 to a yellow residue that
  6. customwas purified by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2302a702b83c454e84c00efd094b899a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

Loading…