Cesium carbonate → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol

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Reaktionsgleichung

Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].Br[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[C:38]([F:41])([F:40])[F:39].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[C:38]([F:39])([F:41])[F:40])[CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To the suspension of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride (300 mg) obtained in Step 2 of Example 1 in 5 ml of toluene, were added 1-bromo-4-fluoro-2-trifluoromethylbenzene (0.198 ml), cesium carbonate (1.42 g), (S)-2,2-bis(diphenylphospino)-1,1-binaphtyl (BINAP; 45.4 mg) and tris(dibenzylideneacetone)dipalladium (1.42 g). The reaction mixture was stirred for about 4 hours at 100° C. under nitrogen atmosphere, was diluted with 30 ml of ethyl acetate, filtered, and concentrated. The resulting residue was purified with column chromatography to give 179 mg of the titled compound.

Aufarbeitung

filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified with column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-28949b92e49a4da1baaf12636fa823fc
Quelldatensatz: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07342027B2

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