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

HRID 1525753Notes

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

Participants

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

custompurged with synthesis gas (carbon monoxide:hydrogen=1:1) to 5 bar
temperaturecooled to ambient temperature
concentrationAfter release of the pressure, the reaction mixture was concentrated under reduced pressure
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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