1-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)- → (2R,3R)-2-(2,4-difluorophenyl)-3-(5',6'-dihydro-2,3'-bipyridin-1'(2'H)-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol

HRID 1009069Notes

Reaction equation

HRID 1009069 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH2:26][NH:27][CH2:28][CH2:29][CH:30]=1.O.O.O.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:10])([C@H:11]([N:27]1[CH2:28][CH2:29][CH:30]=[C:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)[CH2:26]1)[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 183280102-(1,2,5,6-Tetrahydropyridin-3-yl)pyridineHCID 23708903Lithium perchlorate trihydrate

Product 1

HCID 44538715(2R,3R)-2-(2,4-difluorophenyl)-3-(5',6'-dihydro-2,3'-bipyridin-1'(2'H)-yl)-1-(1,2,4-triazol-1-yl)butan-2-olYield 61.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (0.83 g, 3.3 mmol) and 1′,2′,5′,6′-tetrahydro-2,3′-bipyridine (3.51 g, 21.9 mmol) were dissolved in acetonitrile (50 ml), and lithiumperchlorate trihydrate (1.50 g, 9.3 mmol) was added thereto and refluxed for 40 hours. The solvent was evaporated under a reduced pressure, and the thus obtained residue was dissolved in ethyl acetate and washed with water. The solvent was again evaporated under a reduced pressure, and the residue was purified using a silica gel column to obtain 0.87 g of the intended substance (yield 61.9%).

Workup

  1. temperaturerefluxed for 40 hours
  2. customThe solvent was evaporated under a reduced pressure
  3. dissolutionthe thus obtained residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe solvent was again evaporated under a reduced pressure
  6. customthe residue was purified
  7. customto obtain 0.87 g of the intended substance (yield 61.9%)

Sources & evidence

ORD record
ord-686c51868abe4795a54c5eb1c1eaef21
Source dataset
uspto-grants-2011_07
Patent number
US07973056B2

Reaction notes

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