tert-Butanol → Ethyl[4-(6-chloropyridin-3-yl)-1H-1,2,3-triazol-1-yl]acetate

HRID 385940Notes

Reaction equation

HRID 385940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][N:3]=1.[CH2:10]([O:12][C:13](=[O:18])[CH2:14][N:15]=[N+:16]=[N-:17])[CH3:11].CC(O)(C)C>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:10]([O:12][C:13](=[O:18])[CH2:14][N:15]1[CH:9]=[C:8]([C:5]2[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:17]=[N:16]1)[CH3:11]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 69480Acetic acid, azido-, ethyl esterHCID 106542812-Chloro-5-ethynylpyridine

Product 1

HCID 59526155Ethyl[4-(6-chloropyridin-3-yl)-1H-1,2,3-triazol-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent3×

Procedure

2-Chloro-5-ethynylpyridine (100 mg, 0.73 mmol) and ethylazidoacetate (0.41 ml, 0.73 mmol) were taken up in water (1.5 ml) and 2-methylpropan-2-ol (1.5 ml) at room temperature. Aqueous solutions of copper(II) sulfate pentahydrate (9.08 mg, 0.036 mmol) in 1 mL of water and L-sodium ascorbate (28.8 mg, 0.145 mmol) in 1 mL of water were sequentially added, and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with saturated aqueous sodium bicarbonate, and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes) to afford the title compound.

Workup

  1. customat room temperature
  2. customThe reaction was then quenched with saturated aqueous sodium bicarbonate
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e75d9aa5fa72495d94759eff5ef55cbc
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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