Potassium Iodide → 2-(6-{[({(3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

HRID 875199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875199
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH2:25][C:26]1[N:31]=[C:30]([N:32]2[C:40](=[O:41])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]2=[O:42])[CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[N:11][O:12][CH2:25][C:26]2[N:31]=[C:30]([N:32]3[C:33](=[O:42])[C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:40]3=[O:41])[CH:29]=[CH:28][CH:27]=2)[C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 1363312541-(3-bromo-4-methoxyphenyl)-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-N-hydroxymethanimine

Produkt 1

HCID 866507382-(6-{[({(3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dioneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-bromo-4-methoxyphenyl)-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-N-hydroxymethanimine (4.30 g, 10.4 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (3.66 g, 11.5 mmol) in acetonitrile (40 mL) were added cesium carbonate (7.18 g, 22.0 mmol) and potassium iodide (174 mg, 1.05 mmol). After stirring overnight at room temperature, the reaction mixture was diluter with water (100 mL) and ethyl acetate (50 mL). After phase separation and further extraction of the aqueous phase with ethyl acetate (2×30 mL), the combined organic layers were dried over MgSO4 and concentrated in vacuo to afford 2-(6-{[({(3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione as an oil [7.10 g, yield 94%; HPLC/MS: m/z=646 (M+H); log P(HCOOH)=4.78].

Aufarbeitung

  1. customAfter phase separation and further extraction of the aqueous phase with ethyl acetate (2×30 mL)
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b302e15feef746ba9b18cc29ef54ff04
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981111B2

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