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

HRID 386072Notes

Reaction equation

HRID 386072 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:12])([C:10]#[CH:11])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[N:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N+:14]=[N-:15].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:13]1[CH:11]=[C:10]([C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)([OH:12])[CH3:9])[N:15]=[N:14]1)[CH3:21]

Participants

7

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 23667548Sodium AscorbateHCID 595262482-(6-Bromopyridin-2-yl)but-3-yn-2-ol

Product 1

HCID 59526331ethyl{4-[1-(6-bromopyridin-2-yl)-1-hydroxyethyl]-1H-1,2,3-triazol-1-yl}acetate

Reagents, catalysts & solvents 3

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

Procedure

2-(6-Bromopyridin-2-yl)but-3-yn-2-ol (300 mg, 1.33 mmol) and ethyl azidoacetate (0.82 mL, 1.46 mmol) were combined in t-BuOH (3.0 mL) and water (1.0 mL). CuSO4.5H2O (17 mg, 0.066 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (53 mg, 0.27 mmol) in water (1.0 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. Purification by flash chromatography (10-100% EtOAc/hexanes) afforded the title compound as a colorless oil.

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. customPurification by flash chromatography (10-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3847d4a143134679a6f9f2aaa93473db
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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