Bromomethyl acetate → 5,6-Dichloro-1-[6-[1-(acetyloxy)methyl-2-methylpyridinium-3-yl-oxy]pyridin-3-ylcarbamoyl]indoline chloride

HRID 377624

Reaktionsgleichung

Reaktionsgleichung von HRID 377624
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([C:12](=[O:28])[NH:13][C:14]1[CH:15]=[N:16][C:17]([O:20][C:21]3[C:22]([CH3:27])=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:18][CH:19]=1)[CH2:6][CH2:5]2.[C:29]([O:32][CH2:33]Br)(=[O:31])[CH3:30].[B-](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Na+]>C(#N)C>[Cl-:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([C:12](=[O:28])[NH:13][C:14]1[CH:15]=[N:16][C:17]([O:20][C:21]3[C:22]([CH3:27])=[N+:23]([CH2:33][O:32][C:29](=[O:31])[CH3:30])[CH:24]=[CH:25][CH:26]=3)=[CH:18][CH:19]=1)[CH2:6][CH2:5]2

Komponenten

5

Edukt 3

HCID 68536Bromomethyl acetateHCID 2723787Sodium TetraphenylborateHCID 193562595,6-Dichloro-1-[6-(2-methylpyridin-3-yloxy)pyridin-3-ylcarbamoyl]indoline

Produkt 1

HCID 193562665,6-Dichloro-1-[6-[1-(acetyloxy)methyl-2-methylpyridinium-3-yl-oxy]pyridin-3-ylcarbamoyl]indoline chlorideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5,6-Dichloro-1-[6-(2-methylpyridin-3-yloxy)pyridin-3-ylcarbamoyl]indoline (0.25 g, 0.6 mmol) was treated with bromomethyl acetate and sodium tetraphenylboron at reflux in acetonitrile (15 ml) for 10 h according to the procedure described in Example 1 to give the title compound (E3) (0.26 g, 80%) m.p. 125-135° C. which contained approximately 15% starting material as an off-white solid.

Quellen und Nachweise

ORD-Eintrag
ord-346548e1d75c495b94bdc8b45954bf80
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028085

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