Dimethylformamide → 3-(Benzyloxy)-8-chloro-1,5-naphthyridine

HRID 1013778

Reaktionsgleichung

Reaktionsgleichung von HRID 1013778
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C=O)C>C(Cl)Cl>[CH2:20]([O:12][C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[N:5][CH:4]=[CH:3][C:2]=2[Cl:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1357435768-Chloro-1,5-naphthyridin-3-ol

Produkt 1

HCID 673169443-(Benzyloxy)-8-chloro-1,5-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A pyrex reaction tube was charged with 8-chloro-1,5-naphthyridin-3-ol (165 mg, 914 μmol), potassium carbonate (631 mg, 4568 μmol), 1-(chloromethyl)benzene (376 μl, 4568 μmol) and 3.7 mL DMF. The tube was sealed and the mixture was heated at 65° C. for 3 h. The reaction was diluted with DCM and washed with water. The organic portion was dried, filtered, and concentrated. The crude material was purified by silica gel chromatography, 0-25% EtOAc in DCM to provide product as a white solid. MS: [M+H]=271.

Aufarbeitung

  1. customThe tube was sealed
  2. washwashed with water
  3. customThe organic portion was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography, 0-25% EtOAc in DCM
  7. customto provide product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-ac77aa6231c64c7abfe98c05a9ee6a21
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981891B2

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