Sodium Carbonate → 2-[6-(4-Fluoro-phenyl)-pyridazin-3-yloxy]-(1-piperidin-1-yl)-ethanone

HRID 1931386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931386
Br[C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 866381212-(6-Bromo-pyridazin-3-yloxy)-(1-piperidin-1-yl)-ethanone

Produkt 1

HCID 591522632-[6-(4-Fluoro-phenyl)-pyridazin-3-yloxy]-(1-piperidin-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

95 mg (0.326 mmol) of 2-(6-bromo-pyridazin-3-yloxy)-(1-piperidin-1-yl)-ethanone, 46.7 mg (0.334 mmol) 4-fluoro-phenylboronic acid, 11 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium and 0.5 ml of a 1 M aqueous sodium carbonate solution in 15 ml of DME were heated under reflux for 3 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The combined organic phases were dried and evaporated, and the product was purified by RP18 chromatography. Yield: 73 mg.

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customthe product was purified by RP18 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c840eea19cb6420da61baf9cd2efedc0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188291B2

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