Ethyl Acrylate → 7-Fluoro-1,5-naphthyridin-2(1H)-one

HRID 1510613

Reaktionsgleichung

Reaktionsgleichung von HRID 1510613
Br[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(N(CC)CC)C>[NH2:8][C:7]1[C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])=[N:3][CH:4]=[C:5]([F:9])[CH:6]=1.[F:9][C:5]1[CH:6]=[C:7]2[C:2]([CH:12]=[CH:11][C:10](=[O:13])[NH:8]2)=[N:3][CH:4]=1

Komponenten

6

Edukt 2

HCID 8821Ethyl AcrylateHCID 404273672-Bromo-5-fluoropyridin-3-amine

Produkt 2

HCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-oneHCID 68105283ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
147.5 °C

Versuchsvorschrift

To 0.99 g of 2-bromo-5-fluoropyridin-3-amine, 0.67 mL of ethyl acrylate, 3.5 mL of triethylamine, and 0.13 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 145 to 150° C. for 5 hours in a sealed tube. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=100:0 to 90:10 to obtain 0.37 g of ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate and 0.15 g of 7-fluoro-1,5-naphthyridin-2(1H)-one as light brown solids.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resultant residue was purified by flash silica gel column chromatography
  4. washelution with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-5f9e88e7673d4358b8e829909d845ee2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211908B2

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