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Water → Methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

HRID 709796
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 709796
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH2:1]([O:8][C:9]1[C:10]([C:22]2[CH:23]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:21]=2[F:20])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinate

Produkt 1

HCID 117760070Methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinateAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178477754
HCID 178477754, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under a nitrogen atmosphere, to a solution of methyl 5-(benzyloxy)-6chloronicotinate (2.77 g) in 1,4-dioxane (100 mL) were added 2-fluoro-5methoxyphenylboronic acid (2.00 g), potassium carbonate (2.76 g), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (36 mg) and water (10 mL), and the mixture was stirred at 80° C. for 20 hr. The reaction mixture was concentrated, and the residue 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 (petroleum ether/ethyl acetate) to give the title compound (3.50 g) as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8f1257b230414b179698f89fa52ea2b6
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181186B2

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