Ethyl Acetate → 2-(2,4-Difluorophenyl)-3-(pyridin-3-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 1591329Notes

Reaction equation

HRID 1591329 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:11][O:10]1.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1.[Na].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH:12]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:11][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 189565362-(2,4-Difluorophenyl)-2-[1-(pyridin-3-yl)ethyl]oxirane

Product 1

HCID 189565182-(2,4-Difluorophenyl)-3-(pyridin-3-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treatment of the product of part (iii) (4.30 g) with 1H-1,2,4-triazole, sodium salt (3.0 g) in N,N-dimethylformamide (50 ml) according to the method of Example 1(ii), followed by chromatography of the crude product on silica gel using ethyl acetate as eluant, first gave, after combination and evaporation of appropriate fractions, the title compound, diastereoisomeric pair A, (1.13 g), m.p. 113°-114° (from ether).

Workup

  1. customfirst gave
  2. customafter combination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-b577dbf18b5545abb3e9dad799372c70
Source dataset
uspto-grants-1993_04
Patent number
US05206364

Reaction notes

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