Lithium Chloride → 3-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine

HRID 273241

Reaktionsgleichung

Reaktionsgleichung von HRID 273241
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([Br:12])[CH:6]=2.C([Sn](CCCC)(CCCC)[CH:18]=[CH:19][O:20][CH2:21][CH3:22])CCC.[Li+].[Cl-].[F-].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[N:4][CH:3]=[C:2]([CH:18]=[CH:19][O:20][CH2:21][CH3:22])[CH:11]=2

Komponenten

8

Edukt 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 12366583,7-Dibromo-1,5-naphthyridineHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)ethene

Produkt 1

HCID 670823433-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3,7-dibromo-1,5-naphthyridine (0.5 g, 1.74 mmol), tributyl-2-ethoxy-vinylstannane (1.91 mmol, 0.69 g), LiCl (8.7 mmol, 0.37 g) and 0.085 g of PdCl2(PPh3)2 in 50 mL of toluene was heated at 95° C. for 16 hr. After cooling off, 20 mL of a 2 M solution of KF was added to the mixture and stirring was continued for 0.5 hr. The mixture was diluted with 100 mL of CH2Cl2 and washed successively with a saturated solution of sodium bicarbonate, brine and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was chromatographed using 5% MeOH in CH2Cl2 to give the desired material in 55% yield. 1H NMR (CDCl3, 300 MHz) δ 1.40 (m, 3H), 4.05 (m, 2H), 5.85 (s, 1H), 7.25 (s, 1H), 8.15 (m, 1H), 8.55 (m, 1H), 8.85 (m, 2H). MS (ESI) [M+H]+ at 280.

Aufarbeitung

  1. temperatureAfter cooling off
  2. washwashed successively with a saturated solution of sodium bicarbonate, brine and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-8d80b49db92246b7aecd4cc2c5ec4b31
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456196B2

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