3-Pyridinylboronic acid → 1-[4-Fluoro-3-(pyridin-3-yl)phenyl]-5-methyl-1,5-dihydro-imidazo[4,5-c]pyridin-4-one

HRID 2180036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2180036
Br[C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]([CH3:18])[C:13](=[O:19])[C:12]=3[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]([CH3:18])[C:13](=[O:19])[C:12]=3[N:11]=[CH:10]2)=[CH:3][C:2]=1[C:22]1[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=1

Komponenten

3

Edukt 2

HCID 27343783-Pyridinylboronic acidHCID 224902931-(3-Bromo-4-fluorophenyl)-5-methyl-1,5-dihydroimidazo[4,5-c]pyridin-4-one

Produkt 1

HCID 224902911-[4-Fluoro-3-(pyridin-3-yl)phenyl]-5-methyl-1,5-dihydro-imidazo[4,5-c]pyridin-4-oneAusbeute 32 %

Versuchsvorschrift

1-(3-Bromo-4-fluorophenyl)-5-methyl-1,5-dihydroimidazo[4,5-c]pyridin-4-one was coupled to 3-pyridylboronic acid, in the same way as in Example 1, to give 1-[4-fluoro-3-(pyridin-3-yl)phenyl]-5-methyl-1,5-dihydro-imidazo[4,5-c]pyridin-4-one as an off-white solid (50 mg, 32%): δH (400 MHz, CDCl3) 3.69 (3H, s), 6.38 (1H, d, J 7), 7.22 (1H, d, J 7), 7.40-7.49 (3H, m), 7.54 (1H, dd, J 7 and 3), 7.90-7.94 (2H, m), 8.70 (1H, dd, J 5 and 2), 8.84 (1H, s); m/z (ES+) 321 [MH+].

Quellen und Nachweise

ORD-Eintrag
ord-9c1bcfb0ebdf4f6aaacc8d9fc4a96798
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887885B2

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