2-Bromo-6-(bromomethyl)pyridine → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

HRID 227010

Reaktionsgleichung

Reaktionsgleichung von HRID 227010
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:20])[N:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:23].[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[N:26]=1>CN(C)C=O>[Br:24][C:25]1[N:26]=[C:27]([CH2:31][N:11]2[C:12]3[C:17](=[N:16][C:15]([CH3:20])=[CH:14][CH:13]=3)[C:18](=[O:19])[C:9]([C:7](=[O:8])[C:6]3[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([CH3:23])[CH:5]=3)=[CH:10]2)[CH:28]=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 577547063-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

Produkt 1

HCID 577546471-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-oneAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 100 mg (0.324 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one, 97.7 mg (0.389 mmol) of 2-bromo-6-bromomethyl-pyridine, 15.6 mg (0.389 mmol, 60% dispersion in oil), and 1 mL of N,N-dimethylformamide. The crude product was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane and further purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 52.6 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C24H20BrN3O3 [M+H]: 478.07 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.1 min

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography
  2. customfurther purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-f8893307a81e4559b2a925bc13bec401
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

Verknüpfte Notizen

Wird geladen…