Cesium carbonate → 4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline

HRID 1842907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842907
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:10][CH2:9]2)=[C:4]([F:19])[CH:3]=1.[C:20](=[NH:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOC(C)=O.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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Si:12]([O:11][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([N:33]=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:3][C:4]=2[F:19])[CH2:10][CH2:9]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Komponenten

8

Edukt 3

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 70816354(1-(4-Bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane

Produkt 1

HCID 866721464-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroanilineAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a degassed suspension of (1-(4-bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane (4.0 g, 11.59 mmol, 1.0 eq) in toluene (50 mL), was added BINAP (0.261 g, 0.347 mmol, 0.03 eq), benzophenone imine (2.1 g, 11.59 mmol, 1.0 eq) followed by Cs2CO3 (5.64 g, 17.38 mmol, 1.5 eq) in a sealed tube, then was added Pd2(dba)3 (0.138 g, 0.15 mmol, 0.013 eq) and the mixture heated to 100° C. for 8 h. The reaction mixture was diluted with EtOAc (120 mL), washed with water (25 mL×2), brine (25 mL) and dried over Na2SO4 and the solvent was evaporated under vacuum to get 4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline (4.8 g) crude product as a yellow oil (TLC system: EtOAc/PE (1:49), Rf: 0.75).

Aufarbeitung

  1. washwashed with water (25 mL×2), brine (25 mL)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a64b09dae5374eaa85f811ef580c3ca8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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