3-Azidopyridine → tert-Butyl 4-[1-(pyridin-3-yl)-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 2267137Notes

Reaction equation

HRID 2267137 reaction equation
[N:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[N+:2]=[N-:3].[C:10]([C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1)#[CH:11]>C1(C)C=CC=CC=1>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N:1]2[CH:11]=[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)[N:3]=[N:2]2)[CH:5]=1

Participants

4

Reactant 2

HCID 120666873-AzidopyridineHCID 18942198tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 44588461tert-Butyl 4-[1-(pyridin-3-yl)-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylateYield 12.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Azidopyridine (460 mg) prepared in Example 2 and 620 mg of tert-butyl 4-ethynyl-1,2,3,6-tetrahydropyridine-1-carboxylate were dissolved in 8 ml of toluene and the solution was heated to reflux for 20 hours. The reaction solution was returned to room temperature and the solvent was evaporated in vacuo. The resulting residue was separated and produced by a silica gel chromatography (chloroform/methanol=100/1) to give 121 mg of the title compound as a white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 20 hours
  3. customwas returned to room temperature
  4. customthe solvent was evaporated in vacuo
  5. customThe resulting residue was separated
  6. customproduced by a silica gel chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-8cfd7b1cd6c34166ad2660e792c228c6
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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