Cesium carbonate → 1-(4'-{4-[(E)-1-Hydroxy-4-(4-trifluoromethyl-phenyl)-but-3-enyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 1512636

Reaktionsgleichung

[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:31])[CH2:28][CH:29]=[CH2:30])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].I[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:31])[CH2:28]/[CH:29]=[CH:30]/[C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

1-{4′-[4-(1-Hydroxy-but-3-enyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.2518 g, 0.603 mmol), 1-iodo-4-trifluoromethyl-benzene (0.089 mL, 0.603 mmol), and cesium carbonate (0.207 g, 11.38 mmol) were dissolved in ACN (2.6 mL) and the solution was purged with bubbling N2 (g). Palladium(II) acetate (0.008 g, 0.0302 mmol) was added, the reaction vessel was sealed, and the reaction was heated to 85° C. overnight. After cooling, the reaction was submitted to standard aqueous workup to afford the title compound.

Aufarbeitung

customthe solution was purged with bubbling N2 (g)
customthe reaction vessel was sealed
temperatureAfter cooling

Quellen und Nachweise

ORD-Eintrag: ord-1a56b64b748b474fb72bb0ac3baea3ae
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08217066B2

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