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 875199ノート

反応式

HRID 875199 の反応式
[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]

参加物

8

反応物 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

生成物 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)-dione収率 94%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-b302e15feef746ba9b18cc29ef54ff04
出典データセット
uspto-grants-2015_03
特許番号
US08981111B2

反応ノート

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