Hydrochloric Acid → HCID 87293285, compound

HRID 878836Notes

Reaction equation

HRID 878836 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17](I)=[C:16]([O:21][CH:22]([F:24])[F:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[Si](C)(C)N[Si](C)(C)C.C(N(C(C)C)CC)(C)C.Cl.C[N:49](C)[CH:50]=[O:51]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:50]([NH2:49])=[O:51])=[C:16]([O:21][CH:22]([F:24])[F:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 13838HexamethyldisilazaneHCID 81531DiisopropylethylamineHCID 86654465HCID 86654465, compound

Product 1

HCID 87293285HCID 87293285, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
90 °C

Procedure

In a solution of 0.30 g of 5-(3,5-dichlorophenyl)-3-(3-difluoromethoxy-4-iodophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole, 0.80 mL of 1,1,1,3,3,3-hexamethyldisilazane and 0.20 mL of diisopropylethylamine in 10 ml of N,N-dimethylformamide, 0.062 g of 1,1′-bis(diphenylphosphino) ferrocene and 0.013 g of palladium (II) acetate were added, and stirred under carbon monoxide atmosphere at 90° C. for 12 hours and then at room temperature for 3 days. After the completion of the reaction, 10 mL of 1N hydrochloric acid was added, and stirred for 10 minutes, extracted with ethyl acetate (10 mL×2). The combined organic phases were washed with water, and then dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (2:3) to obtain 0.30 g of the aimed product as yellow resinous substance.

Workup

  1. waitat room temperature for 3 days
  2. additionwas added
  3. stirringstirred for 10 minutes
  4. extractionextracted with ethyl acetate (10 mL×2)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-bb4716866a854551bd801f23e8b4a94e
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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