Potassium Carbonate → 7-chloro-3-(3,5-dimethoxyphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one

HRID 524052

Reaktionsgleichung

Reaktionsgleichung von HRID 524052
[Cl:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[C:5]([CH:6]=O)=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:22][C:23](OC)=[O:24])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]2[C:5]([CH:6]=[C:22]([C:16]3[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:14]([O:13][CH3:12])[CH:15]=3)[C:23](=[O:24])[N:10]2[CH3:11])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 592191Methyl 3,5-dimethoxyphenylacetateHCID 234345716-Chloro-4-(methylamino)nicotinaldehyde

Produkt 1

HCID 867135767-chloro-3-(3,5-dimethoxyphenyl)-1-methyl-1,6-naphthyridin-2(1H)-oneAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 6-chloro-4-(methylamino)nicotinaldehyde (3.7 g, 21.7 mmol), methyl 2-(3,5-dimethoxyphenyl)acetate (4.5 g, 21.7 mmol) and potassium carbonate (9.0 g, 65.1 mmol) in N,N-dimethylformamide (30 mL) was heated at 105° C. for 5 h. LCMS showed the reaction was completed. The reaction was cooled to RT, quenched with water (200 mL), and filtered. The filtration cake was washed by petroleum ether (50 mL) and ethyl acetate (50 mL) to afford the title compound (5.8 g, 77%) as a yellow solid. MS (ES+) C18H19ClN2O3 requires: 346, 348. found: 347, 349 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (200 mL)
  3. filtrationfiltered
  4. washThe filtration cake was washed by petroleum ether (50 mL) and ethyl acetate (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9cf9ea22fa634854a14f4dd1149174fa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340514B2

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