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Method for preparing 3-imino isoindoline ketone compounds

A compound, aryl technology, applied in the field of organic synthesis, can solve the problems of limited application, long reaction time, etc.

Active Publication Date: 2016-02-03
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also, the reaction requires higher temperature and longer reaction time (150°C, 24h), which limits the further application of this method [Y.Kuninobu et al., Angew.Chem.Int.Ed.2013,52,11879–11883]

Method used

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  • Method for preparing 3-imino isoindoline ketone compounds
  • Method for preparing 3-imino isoindoline ketone compounds
  • Method for preparing 3-imino isoindoline ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Example 1 Trans-2-tert-butyl-3-methoxyiminoisoindolinone (3a)

[0095]

[0096] Under air (air) (1atm), add amide compound 1a15.1mg (0.10mmol), tert-butylisonitrile 18μL, (0.15mmol), Pd in ​​a 15mL reaction tube 2 (dba) 32.3mg (0.0025mmol), 1mL of 1,4-dioxane (dioxane), mix well, and react at 80°C for 0.5 hours. After the reaction was completed, it was cooled to room temperature and concentrated to obtain a crude product. The crude product was separated with a preparative plate (the volume ratio of petroleum ether to ethyl acetate was 20:1), and 21.7 mg of the product trans-2-tert-butyl-3-methoxyiminooxyisoindolinone (94% ); 1 HNMR (400MHz, CDCl 3 )δ8.26–8.24(m,1H),7.77–7.75(m,1H),7.58–7.50(m,2H),4.06(s,3H),1.76(s,9H); 13 CNMR (100MHz, CDCl 3 )δ167.33, 149.98, 132.78, 131.74, 131.10, 128.53, 127.73, 122.65, 63.24, 58.65, 29.60; HRMS (ESI-TOF) m / zCalcdforC 13 h 17 N 2 o 2 (M+H) + :233.1285,found:233.1276.

Embodiment 2

[0097] Example 2 trans-7-methyl-2-tert-butyl-3-methoxyiminoisoindolinone (3b)

[0098]

[0099] The procedure was similar to that of Example 1, except that the corresponding starting compound 1b was used instead of compound 1a. Reaction time 10 hours, productive rate 67%; 1 HNMR (400MHz, CDCl 3 )δ8.13(d, J=7.6Hz, 1H), 7.43(t, J=7.6Hz, 1H), 7.28(d, J=7.6Hz, 1H), 4.05(s, 3H), 2.67(s, 3H), 1.75(s, 9H); 13 CNMR (100MHz, CDCl 3 )δ168.37, 149.80, 137.14, 133.71, 132.35, 129.10, 128.40, 125.51, 63.30, 58.58, 29.73, 17.90; HRMS (ESI-TOF) m / zCalcdforC 14 h 19 N 2 o 2 (M+H) + :247.1441,found:247.1451.

Embodiment 3

[0100] Example 3 Trans-6-methyl-2-tert-butyl-3-methoxyiminoisoindolinone (3c)

[0101]

[0102] The procedure was similar to that of Example 1, except that the corresponding starting compound 1c was used instead of compound 1a. Reaction time 0.5 hour, productive rate 90%; 1 HNMR (400MHz, CDCl 3 )δ8.11(d,J=7.6Hz,1H),7.55(s,1H),7.36(dd,J=8.0,0.8Hz,1H),4.05(s,3H),2.44(s,3H), 1.75(s,9H); 13 CNMR (100MHz, CDCl 3 )δ167.63, 150.25, 141.86, 133.63, 132.12, 127.58, 126.18, 123.09, 63.23, 58.66, 29.70, 21.81; HRMS (ESI-TOF) m / zCalcdforC 14 h 19 N 2 o 2 (M+H) + :247.1441,found:247.1452.

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Abstract

The invention relates to a method for preparing 3-imino isoindoline ketone compounds and particularly discloses a method for preparing the 3-imino isoindoline ketone compounds through the activation method of palladium catalysis of the C-H bond, wherein the 3-imino isoindoline ketone compounds are as shown in the formula I (refer to the Specification). The method comprises the following steps: under the existence of an inert solvent, under the catalysis of a palladium catalyst, and under the action of an oxidizing agent, the compounds II (N-alkoxy amide compounds) and the compounds III (isonitrile compounds) react to obtain the compounds I, wherein the structures of the compounds I, compounds II and compounds III are as shown in the Specification. The method is high in efficiency, excellent in selectivity, economical, environment friendly, fewer in steps, simple and convenient to operate, wide in application range of substrates, and excellent in atom economy. The invention further provides a method for further conversion of the compounds I.

Description

technical field [0001] The invention belongs to the field of organic synthesis. Specifically, the present invention relates to a method for preparing 3-iminoisoindolinone compounds, more specifically, to a method for preparing 3-iminoisoindolinones by palladium-catalyzed carbon-hydrogen bond insertion compound method. Background technique [0002] Nitrogen-containing heterocycles are a common class of compounds in organic chemistry and widely exist in natural products and molecules with biological activity. As an important class of nitrogen-containing heterocyclic rings, 3-imino oxidized isoindolinone compounds are due to their important biological activities, such as blood lipid lowering, anti-inflammatory analgesic and anti-tumor effects [L.Butner et al., Biomed & Pharmacother.1996 , 50, 290-296; A.R.K.Murthy et al., Pharm.Res.1987, 4, 21-27; I.H.Hall et al., Anti-Cancer Drugs, 1994, 5, 207-212], thus receiving widespread attention. [0003] At present, there are releva...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/50C07D209/68C07D491/048C07D495/04C07D487/04C07D513/04C07D471/04C07D401/04C07D403/04C07D413/04C07D417/04C07D209/46C07F9/572C07C227/22C07C229/38C07C67/20C07C69/80C07C259/10C07C231/12C07C233/65
Inventor 余金权戴辉雄刘悦进徐辉孔维俊商明
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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