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Cesium carbonate → 4'-[(1S,2R)-2-(2-Hydroxyethyl)cycloprop-1-yl]biphenyl-4-carbonitrile

HRID 515048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 515048
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15].C([O-])([O-])=O.[Cs+].[Cs+]>C(O)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:13][CH2:12][CH2:11][C@H:9]1[CH2:10][C@@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1
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Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 27343264-Cyanophenylboronic acidHCID 684071222-[(1R,2S)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

Produkt 1

HCID 684076744'-[(1S,2R)-2-(2-Hydroxyethyl)cycloprop-1-yl]biphenyl-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, Verbindung
Katalysator
HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of the product of Example 28E (2-[(1R,2S)-2-(4-bromophenyl)cycloprop-1-yl]ethanol), 4-cyanophenylboronic acid [CAS 126747-14-6] (2 equivalents), Pd(PPh3)2Cl2, and Cs2CO3 in isopropanol under N2 was stirred at reflux overnight. The mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous NaHCO3 and then with brine. The organic layer was then dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by chromatography on silica gel eluted with 4:1 hexanes/ethyl acetate to provide the title compound.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customThe mixture was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by chromatography on silica gel
  8. washeluted with 4:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4d5003c5387e48bf9c8ea8063b9ce60a
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108948B2

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