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Water → 5-(4-Chloro-phenyl)-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester

HRID 1929913
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1929913
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9](Br)[C:8]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:7][C:6]=1[C:17]([F:20])([F:19])[F:18])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[C:8]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:7][C:6]=1[C:17]([F:20])([F:19])[F:18])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 675049975-Bromo-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester

Produkt 1

HCID 675046855-(4-Chloro-phenyl)-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl esterAusbeute 114,3 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Bromo-6-cyclopropylmethoxy-2-trifluoromethyl-nicotinic acid ethyl ester (0.3 g, 0.81 mmol) was dissolved in dioxane (1.6 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (33 mg, 0.04 mmol), 4-chlorophenylboronic acid (197 mg, 1.2 mmol) and sodium carbonate solution (2M, 1.2 mL). This mixture was heated to 80° C. for 5 h and cooled to room temperature. Water (150 mL) was added, the phases were separated and the water mixture was extracted with ethylacetate. Organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo. The residue was purified by flash chromatography on silica (dichloromethane/methanol, 4:1) to give the title compound (0.37 g) as light yellow oil; MS (ISP) 400.1 (M+H)+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customthe phases were separated
  3. extractionthe water mixture was extracted with ethylacetate
  4. dry with materialdried with MgSO4
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by flash chromatography on silica (dichloromethane/methanol, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-e9cf95d844e04e0c9c844ac2ad3a30c6
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188093B2

Notizen zur Reaktion

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