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Cesium carbonate → Ethyl 2-(5-chloro-6-(cyclopropylmethoxy)-4'-(trifluoromethyl)biphenyl-3-yl)-4-methoxybutanoate

HRID 1512531
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512531
Br[C:2]1[CH:3]=[C:4]([CH:14]([CH2:20][CH2:21][O:22][CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.C([O-])([O-])=O.[Cs+].[Cs+].[F:30][C:31]([F:42])([F:41])[C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>CN(C=O)C.O>[Cl:13][C:6]1[CH:5]=[C:4]([CH:14]([CH2:20][CH2:21][O:22][CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=[C:2]([C:35]2[CH:36]=[CH:37][C:32]([C:31]([F:42])([F:41])[F:30])=[CH:33][CH:34]=2)[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57995612Ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)-phenyl)-4-methoxybutanoate

Produkt 1

HCID 57995624Ethyl 2-(5-chloro-6-(cyclopropylmethoxy)-4'-(trifluoromethyl)biphenyl-3-yl)-4-methoxybutanoateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)-phenyl)-4-methoxybutanoate (2.3 g, 5.660 mmol) in a mixture of DMF (50 mL) and water (5 mL) were added Cs2CO3 (6.4 g, 19.815 mmol), Pd(TPP)4 (1.3 g, 1.120 mmol) and 4-(trifluoromethyl)phenyl boronic acid (1.29 g, 6.780 mmol) at RT under N2 atmosphere and the resulting mixture was stirred at 80° C. for 14 h. After completion of starting material (by TLC), filtered off the catalyst and celite bed was washed with EtOAc and extracted with EtOAc (3×100 mL). Combined organic layers were washed with water (3×50 mL), brine and dried over anhydrous Na2SO4. After filtration and concentration under reduced pressure, the crude material was purified by column chromatography to afford ethyl 2-(5-chloro-6-(cyclopropylmethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)-4-methoxybutanoate (1.2 g) as an off white solid.

Aufarbeitung

  1. filtrationAfter completion of starting material (by TLC), filtered off the catalyst and celite bed
  2. washwas washed with EtOAc
  3. extractionextracted with EtOAc (3×100 mL)
  4. washCombined organic layers were washed with water (3×50 mL), brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and concentration under reduced pressure
  7. customthe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4e84e48d37584ffab36b5e86e6e3c60c
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217064B2

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