Sodium Azide → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-[1-(3-trifluoromethyl-benzyl)-1H-[1,2,3]triazol-4-yl]-methanol

HRID 1624420Notes

Reaction equation

HRID 1624420 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:28][N:27]=[C:26]([CH3:29])[C:25]=2[CH:30]([OH:33])[C:31]#[CH:32])=[CH:20][CH:19]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CS(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[O:28][N:27]=[C:26]([CH3:29])[C:25]=2[CH:30]([C:31]2[N:13]=[N:14][N:15]([CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=3)[CH:32]=2)[OH:33])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 23667548Sodium AscorbateHCID 866524111-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-prop-2-yn-1-ol

Product 1

HCID 66579377[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-[1-(3-trifluoromethyl-benzyl)-1H-[1,2,3]triazol-4-yl]-methanol

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

1-Bromomethyl-3-trifluoromethyl-benzene (0.0491 g, 0.205 mmol) and sodium azide (0.0222 g, 0.342 mmol) were combined in DMSO and stirred at room temperature for 2 hours. Then, 1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-prop-2-yn-1-ol (0.500 g, 0.171 mmol), copper(II)sulfate pentahydrate (0.0043 g, 0.017 mmol) and sodium ascorbate (0.0034 g, 0.017 mmol) were added and the reaction stirred at room temperature for 2 days. The reaction was submitted to standard aqueous workup and purified on silica gel to afford the title compound.

Workup

  1. stirringthe reaction stirred at room temperature for 2 days
  2. custompurified on silica gel

Sources & evidence

ORD record
ord-71cdd0432c40459ab54afb5ca32f0364
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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