Sodium Bicarbonate → HCID 73057752, Verbindung

HRID 2207329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207329
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:18])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[N:13][CH:12]=3)=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.C(=O)([O-])O.[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:19][N:20]1[CH:24]=[C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:9][C:10](=[O:18])[C:11]4[C:16]([CH:17]=3)=[CH:15][CH:14]=[N:13][CH:12]=4)=[CH:4][CH:3]=2)[CH:22]=[N:21]1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 90040060HCID 90040060, Verbindung

Produkt 1

HCID 73057752HCID 73057752, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A suspension of 3-(4-bromo-phenyl)-2H-[2,7]naphthyridin-1-one (63.2 mg, 0.210 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (65.5 mg, 0.32 mmol) and sodium hydrogen carbonate (21.2 mg, 0.25 mmol) in DMF (1 ml) and water (0.25 ml) is flushed with nitrogen and heated to 40° C. Then bis(triphenylphosphine)-palladium(II)-chloride (3.0 mg, 0.004 mmol) is added. The reaction mixture is heated to 80° C. and stirred at this temperature for 20 hours. The mixture is allowed to cool to room temperature and excess water is added. The resulting precipitate is filtered off washed with water and dried under vacuum to afford 3-[4-(1-methyl-1H-pyrazol-4-yl)-phenyl]-2H-[2,7]naphthyridin-1-one as olive green solid; HPLC/MS 1.33 min (A), [M+H] 303;

Aufarbeitung

  1. customis flushed with nitrogen
  2. temperatureThe reaction mixture is heated to 80° C.
  3. temperatureto cool to room temperature
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a161fbb6afd6410b95c04c99a7c2c691
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376433B2

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