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N,N,N',N'-Tetramethylethylenediamine → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde

HRID 1525753
Notes
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Reaction equation

HRID 1525753 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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:47][C:29]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CN(C)CCN(C)C>CN(C=O)C>[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]([CH:29]=[O:47])=[C:3]([CH3:25])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehydeYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A reaction autoclave was charged with 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (0.10 g, 0.22 mmol), palladium dichloride cyclooctadiene complex (1.6 mg, 2.5 mol-%), xanthphos (9.7 mg, 7.5 mol-%), N,N,N′,N′-tetramethylethylene diamine (19.3 mg, 0.75 equiv.) and DMF (2 mL) and purged with synthesis gas (carbon monoxide:hydrogen=1:1) to 5 bar. The reaction autoclave was heated to 100° C. for 16 h and then cooled to ambient temperature. After release of the pressure, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel to yield the title compound (13 mg, 15%).

Workup

  1. custompurged with synthesis gas (carbon monoxide:hydrogen=1:1) to 5 bar
  2. temperaturecooled to ambient temperature
  3. concentrationAfter release of the pressure, the reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-499d5e87306c4603a0b467113f159c37
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085541B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes