3-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride → [1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-[3-(2-chloro-6-fluorophenyl)-5-methyl-isoxazol-4-yl]-methanone

HRID 349277Notes

Reaction equation

HRID 349277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14](Cl)=[O:15])=[C:12]([CH3:17])[O:11][N:10]=1.[F:18][C:19]([F:56])([F:55])[C:20]1[CH:21]=[C:22]([CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1)[CH2:23][N:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:27]([Sn](CCCC)(CCCC)CCCC)[N:26]=[N:25]1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:56][C:19]([F:18])([F:55])[C:20]1[CH:21]=[C:22]([CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1)[CH2:23][N:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:27]([C:14]([C:13]2[C:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:10][O:11][C:12]=2[CH3:17])=[O:15])[N:26]=[N:25]1

Participants

5

Reactant 2

HCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 866012141-(3,5-bis-trifluoromethyl-benzyl)-4-(tri-n-butylstannanyl)-5-phenyl-1H-[1,2,3]triazole

Product 1

HCID 58804047[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-[3-(2-chloro-6-fluorophenyl)-5-methyl-isoxazol-4-yl]-methanoneYield 50%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl chloride (187 mg, 0.681 mmol) and 1-(3,5-bis-trifluoromethyl-benzyl)-4-(tri-n-butylstannanyl)-5-phenyl-1H-[1,2,3]triazole (300 mg, 0.454 mmol) in the presence of PdCl2(PPh3)2 (32 mg) in degassed 1,4-dioxane (3.0 mL) at 80° C. After 18 h., concentrate in vacuo and purify the residue by chromatography on silica gel to provide the title compound (50% yield) as a light yellow foam. MS (ES) 609.0 (M++1); TLC Rf=0.1 (6% acetone in hexanes).

Workup

  1. temperatureHeat
  2. concentrationconcentrate in vacuo
  3. custompurify the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-eff5b4a9c30b443399ae5607a30285b0
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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