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Potassium Carbonate → Ethyl 6-bromo-1-(1,3-dimethoxypropan-2-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

HRID 1047166
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1047166
[Br:1][C:2]1[CH:3]=[C:4]([C:17](F)=[CH:18][N:19]=1)[C:5]([C:7](=[CH:13]N(C)C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].[CH3:21][O:22][CH2:23][CH:24]([NH2:28])[CH2:25][O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][N:19]=1)[N:28]([CH:24]([CH2:25][O:26][CH3:27])[CH2:23][O:22][CH3:21])[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15141601,3-Dimethoxypropan-2-amineHCID 86665047Ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate2×

Produkt 1

HCID 86665048Ethyl 6-bromo-1-(1,3-dimethoxypropan-2-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylateAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 65, 1 g, 2.9 mmol, 1 equiv.) in THF (7 mL) was added 1,3-dimethoxypropan-2-amine (451 mL, 2.9 mmol, 1 equiv.). This reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was concentrated under reduced pressure and re-suspended in DMF (7 mL). Potassium carbonate (1.2 g, 8.69 mmol, 3 equiv.) was added, and the reaction mixture was stirred at 70° C. for 3 h. The reaction mixture was cooled to room temperature and quenched with water. 1 N HCl was added until pH 4-5 was reached. The precipitate was washed with water and hexanes and dried to provide ethyl 6-bromo-1-(1,3-dimethoxypropan-2-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate as a solid (963 mg, 83%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe reaction mixture was stirred at 70° C. for 3 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched with water
  5. addition1 N HCl was added until pH 4-5
  6. washThe precipitate was washed with water and hexanes
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ef3e54a764ed4b948fb48d7f9749e2bc
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08569484B2

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