Triphenylphosphine → 6-(2-cyclohexylethoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331323

Reaktionsgleichung

Reaktionsgleichung von HRID 331323
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]=2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.Br[C:27]1[C:28](=O)[C:29]2[C:34](C=1C1C=CC=CC=1)=[CH:33][CH:32]=[C:31](O)[CH:30]=2.C1(CCO)CCCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH:29]1([CH2:28][CH2:27][O:18][C:14]2[CH:13]=[C:12]3[C:17]([C:9]([C:4]4[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=4)=[C:10]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:11]3=[O:19])=[CH:16][CH:15]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Komponenten

6

Edukt 5

HCID 11776TriphenylphosphineHCID 205082-CyclohexylethanolHCID 5363146Diisopropyl azodicarboxylateHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703174323-(3,5-difluorophenyl)-6-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one

Produkt 1

HCID 510020446-(2-cyclohexylethoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-oneAusbeute 26 %

Versuchsvorschrift

The procedure of Step 6 of Example 1 was repeated except for using 3-(3,5-difluorophenyl)-6-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one obtained in Step 1 of Example 64 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, 2-cyclohexylethanol (2.0 eq) instead of 4-(2-hydroxyethyl)morpholine, using 2 equivalents of PPh3 and DIAD, being stirred for 48 h, and being purified by prep. HPLC (20% H2O/CH3CN) to provide the title compound (26%).

Aufarbeitung

  1. custombeing purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-b732b1eb2284406d9ffb26a6fa07d641
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877747B2

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