Acetic acid, azido-, ethyl ester → ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

HRID 386062

Reaction equation

HRID 386062 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[N:3]=1.[N:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:11]=[N-:12].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[N:3]=2)[N:12]=[N:11]1)[CH3:18]

Participants

7

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 129705322-Bromo-6-ethynylpyridineHCID 23667548Sodium Ascorbate

Product 1

HCID 59525977ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

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 ethyl azidoacetate (1.08 ml, 1.92 mmol) were combined in t-BuOH (4.0 mL) and water (2.0 mL). CuSO4.5H2O (24 mg, 0.096 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (76 mg, 0.39 mmol) in water (1.0 mL). The reaction was stirred at room temperature for 5 h, 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 (0-30% 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 (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c07ac8fa129843fba3c3213505dc47fb
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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