Water → HCID 86631560, compound

HRID 885809Notes

Reaction equation

HRID 885809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[N:16][C:17](Cl)=[C:18]([Cl:20])[CH:19]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.N.O.[CH3:29][N:30](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:20][C:18]1[CH:19]=[C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:22]([F:23])([F:24])[F:25])[O:13][N:12]=2)[CH:15]=[N:16][C:17]=1[C:29]#[N:30]

Participants

7

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 12896473Azane;hydrateHCID 71615482HCID 71615482, compound

Product 1

HCID 86631560HCID 86631560, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

In a solution of 1.40 g of 5-(3,5-dichlorophenyl)-3-(5,6-dichloro-3-pyridyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 mL of N,N-dimethylacetamide, 0.075 g of zinc cyanide and 0.37 g of tetrakis(triphenylphosphine) palladium(0) were added, and stirred at 80° C. to 120° C. for 4.5 hours under nitrogen atmosphere. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 5 mL of ammonia water and 50 mL of water were added, and extracted with ethyl acetate (50 mL×1). The organic phase were dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and the solvent was distilled off under reduced pressure. The residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that was eluted with ethyl acetate-hexane (gradient of 1:8 to 1:3) to obtain 1.20 g of the aimed products as yellow resinous substance.

Workup

  1. customAfter the completion of the reaction
  2. waitthe reaction mixture was left
  3. extractionextracted with ethyl acetate (50 mL×1)
  4. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that
  7. washwas eluted with ethyl acetate-hexane (gradient of 1:8 to 1:3)

Sources & evidence

ORD record
ord-690f3503e8af43fd886e83e5d48e3268
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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