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

HRID 2267144Notes

Reaction equation

HRID 2267144 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=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:7]1[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][CH:6]=1

Participants

4

Reactant 2

HCID 113324494-AzidopyridineHCID 18942198tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 44588462tert-butyl 4-[1-(pyridin-4-yl)-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylateYield 13.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Azidopyridine (140 mg) prepared in the above 1) and 207 mg of tert-butyl 4-ethynyl-1,2,3,6-tetrahydropyridine-1-carboxylate were dissolved in 3 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 44 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-7145e0386db94787a50e2a07c0f9da01
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

Loading…