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 875199노트

반응식

HRID 875199 반응식
[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]

참가 물질

8

반응물 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

생성물 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)-dione수율 94%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-b302e15feef746ba9b18cc29ef54ff04
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981111B2

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