Hydrochloric Acid → HCID 67124168, compound

HRID 1464900Notes

Reaction equation

HRID 1464900 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25].C(O)C[CH2:28][CH2:29][OH:30].C(OC=C)=C.C1(C(N)C2CCCCC2)CCCCC1.Cl>[Pd].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.C(O)CCC>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:29](=[O:30])[CH3:28])=[C:3]([CH3:25])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 22660526HCID 22660526, compoundHCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 67124168HCID 67124168, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (500 mg), 1,4-butandiol-monovinyl ether (385 mg), 1,3-bis(diphenylphosphine)propane (dppp, 9 mg), palladium on charcoal (10%, 23 mg), dicylohexylmethylamine (259 mg) and n-butanol (3 mL) were stirred under an atmosphere of nitrogen at reflux over night. After cooling, ethyl acetate (30 mL) and aqueous hydrochloric acid (1 M, 20 mL) were added and the mixture was stirred at room temperature for 1 h. After filtration, the layers were separated, the organic layer was extracted with 1 M HCl, dried (Na2SO4) and evaporated in vacuum. Purification of the residue on silica gel afforded the title compound (270 mg, 60%).

Workup

  1. temperatureat reflux over night
  2. temperatureAfter cooling
  3. stirringthe mixture was stirred at room temperature for 1 h
  4. filtrationAfter filtration
  5. customthe layers were separated
  6. extractionthe organic layer was extracted with 1 M HCl
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuum
  9. customPurification of the residue on silica gel

Sources & evidence

ORD record
ord-1a714dd0f8c34c219a5d67336a747b1b
Source dataset
uspto-grants-2015_04
Patent number
US08999889B2

Reaction notes

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