Sodium Carbonate → 4-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one

HRID 1478545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478545
C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][N:18]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH:19]=2)O1.Br[C:28]1[N:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[CH:32]=[C:31]2[NH:39][O:40][CH2:41][CH3:42]>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(OCC)(=O)C.O.C(#N)C>[CH2:41]([O:40][NH:39][C:31]1[C:30]2[C:35](=[CH:36][CH:37]=[C:28]([C:15]3[CH:16]=[N:17][N:18]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:19]=3)[N:29]=2)[NH:34][C:33](=[O:38])[CH:32]=1)[CH3:42]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridineHCID 900431286-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one

Produkt 1

HCID 900440984-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To Na2CO3 (151 mg, 1.41 mmol) was added water (1.5 ml) and acetonitrile (2 ml) and the solution was degassed for 5 min with argon. 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]pyridine (84 mg, 0.31 mmol), 6-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one (80 mg, 0.28 mmol) and Pd(dppf)Cl2 (10 mg, 0.014 mmol) were added sequentially followed by addition of acetonitrile (2 ml). The mixture was stirred at 100° C. for 15 h then allowed to cool to ambient temperature. Water and ethyl acetate were added then the phases were separated. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification by chromatography afforded of 4-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one.

Aufarbeitung

  1. customthe solution was degassed for 5 min with argon
  2. temperatureto cool to ambient temperature
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f56a2a60e36e4a8c9b8b3faea3cbdef6
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403845B2

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