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Sodium Carbonate → Ethyl 3-cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4''-(trifluoromethyl)-1,1':2',1''-terphenyl-4'-yl)oxy)methyl)phenyl)propanoate

HRID 1049452
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1049452
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21](OS(C(F)(F)F)(=O)=O)[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[F:42][C:43]([F:54])([F:53])[C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[C:21]([C:47]4[CH:48]=[CH:49][C:44]([C:43]([F:54])([F:53])[F:42])=[CH:45][CH:46]=4)[C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[CH:23][CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117759787Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate

Produkt 1

HCID 117760114
Ethyl 3-cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4''-(trifluoromethyl)-1,1':2',1''-terphenyl-4'-yl)oxy)methyl)phenyl)propanoate
Ausbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Under a nitrogen atmosphere, to a solution of ethyl 3-cyclopropyl-3-(3-(((2′-fluoro-5′-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate (173 mg) in toluene (5.0 mL) were added 4-(trifluoromethyl)phenylboronic acid (157 mg), tris(dibenzylideneacetone)dipalladium(0) (20 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (39 mg) and 2.0 M aqueous sodium carbonate solution (0.43 mL), and the mixture was stirred at 90° C. for 15 hr. The reaction mixture was filtered through celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (97 mg) as a colorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite, water
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2a75403eef344e93b7c310d0027d122c
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09382188B2

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