Month: January 2021

Reference of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a flask equipped with mechanical stirrer, thermometer, condenser and nitrogen inlet was added 6-chloro-5-(2-chloroethyl)-l,3-dihydro-2H-indol-2- one (21.6 g, 94 mmol), 3-(l-piperazinyl)-l,2-benzoisothiazole hydrochloride (24 g, 94 mmol), sodium carbonate (29.9 g, 282 mmol) and l-methyl-2- pyrrolidinone (NMP) (96 ml) and the mixture was heated to 130-1350C under nitrogen for about 24 hrs. The mixture was cooled to 40-450C and poured into water. The suspension was cooled and the product was collected by filtration on a Buchner funnel, the filter cake was rinsed with water at 20- 250C and the damp product was transferred to a drying oven and dried in vacuo. This afforded 34.2 g (88.2% yield) of crude ziprasidone. The IR (KBr) and NMR spectra were consistent with those of reference ziprasidone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Patent; APOTEX PHARMACHEM INC.; WO2006/47893; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3485-84-5, The chemical industry reduces the impact on the environment during synthesis 3485-84-5, name is N-Vinylphthalimide, I believe this compound will play a more active role in future production and life.

General procedure: General procedure B: To a dried glass tube, Togni reagent 2 (99mg, 0.3mmol, 1.5equiv), (L3)CuBr (10mg, 0.02mmol, 0.1equiv) and CH3CN (1.0mL) were added under N2 atmosphere, followed by substrate 1 (0.2mmol, 1.0equiv) and TMSCN (54muL, 0.4mmol, 2.0equiv). After the reaction mixture was stirred at room temperature for 0.5h, the mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel with a gradient eluent of petroleum ether and ethyl acetate to afford the product. General procedure B: Pale yellow solid; 46.6mg, 87%; 1H NMR (400MHz, CDCl3): delta 7.94 (dd, J=5.2, 3.2Hz, 2H), 7.82 (dd, J=5.2, 3.2Hz, 2H), 5.54 (dd, J=8.4, 5.2Hz, 1H), 3.33-3.17 (m, 1H), 3.06-2.94 (m, 1H); 13C NMR (100MHz, CDCl3): delta 165.5, 135.1, 131.0, 124.3, 124.0 (q, J=276.3Hz), 114.0, 35.0 (q, J=30.0Hz), 33.9 (q, J=3.8Hz); 19F NMR (376MHz, CDCl3): delta -65.1 (t, J=10.0Hz); HRMS (EI), calcd. for C12H7F3N2O2 268.0460 [M]+, found 268.0456.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Vinylphthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liang, Zhaoli; Wang, Fei; Chen, Pinhong; Liu, Guosheng; Journal of Fluorine Chemistry; vol. 167; (2014); p. 55 – 60;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of phthalic anhydride (1 mmol), isatin (1 mmol), malononitrile(1 mmol), hydrazine (1 mmol), and Fe3O4dipyridineMNPs (0.0008 g) was stirred at room temperature under solvent free conditions for 50 min. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed,EtOH was added to the reaction mixture and the Fe3O4methyleneMNPs was separated by external magnet. Then the solvent was removed from solution under reduced pressure and the resultingproduct purified by recrystallization using ethanol.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Review; Sadeghzadeh, Seyed Mohsen; Nasseri, Mohammad Ali; Catalysis Today; vol. 217; (2013); p. 80 – 85;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, A common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The intermediate compound 4 (0.05 mol) was slowly added to 30 ml of 0 C concentrated H2SO4,Control the temperature does not exceed 12 C; added, ice bath conditions slowly add mixed acid (fuming nitric acid / concentrated sulfuric acid = 1/1) 15ml, remove the ice bath, 55 C heating and stirring for 12 hours. The reaction solution was poured into 3 times of ice water, and the mixture was stirred while stirring, and the solid was filtered. The filter cake was washed three times with 100 ml of water and recrystallized from 95% ethanol to give intermediate 11 as a pale yellow solid in 16%

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 261732-38-1 as follows. Application In Synthesis of tert-Butyl 5-bromoindoline-1-carboxylate

A solution of the title B compound, 5-bromo-2, 3-DIHYDRO-INDOLE-1-CARBOXYLIC acid tert-butyl ester (15.86 g, 53.22 mmol) in 500 mL THF is cooled TO-73C and treated with n-butyllithium (1.6 M in hexanes, 53.22 mL, 85.15 MMOL). After 15 min AT-73C, dry COs is bubbled through the solution for 40 min. The reaction is kept AT-73C for 1 h, warmed to 0C for 1 h, and then warmed to RT for 1 h. The mixture is poured into 1 N aqueous HCI and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with brine, dried over anhydrous MGS04, and concentrated to afford of 2, 3-dihydro-indole-1, 5-dicarboxylic acid 1-tert-butyl ester as an white solid : NMR (DMSO-D6) 1.51 (s, 9H), 3.10 (t, 2H, J = 8.75), 3. 69 (t, 2H, J = 8.80), 7.73-7. 79 (m, 3 H), 12.62 (br s, 1 H).

According to the analysis of related databases, 261732-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65351; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 114041-16-6,Some common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 17 N-(2-tert-butoxybenzyl)-6-(5,6-dimethoxyisoindolin-2-yl)-N-(pyridin-2-ylmethyl)hexan-1-amine [13] The same procedure as described for compound 11 was applied to starting material 10 (0.428 g, 0.988 mmol) and 5,6-dimethoxyisoindoline (0.175 g, 0.975 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as pale yellow oil (60%). 1H NMR (CDCl3) delta 8.446 (dd, 1H, Ar), 7.72 (m, 3H, Ar), 7.062 (m, 2H, Ar), 6.981 (ddd, 2H, Ar), 6.888 (s, 2H, Ar), 3.816 (s, 4H, -CH2-CH2-), 3.792 (s, 6H, -OCH3-), 3.714 (s, 2H, -CH2-), 3.637 (s, 2H, -CH2-), 2.611 (t, 2H, -CH2-), 2.436 (t, 2H, -CH2-), 1.503 (m, 4H, -CH2-CH2-), 1.319 (s, 9H, -C(CH3)3), 1.275 (m, 4H, -CH2-CH2-). Mass Spec.=531.73 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethoxyisoindoline, its application will become more common.

Reference:
Patent; President and Fellows of Harvard College; US2012/269724; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of isatin derivatives 1 (1 mmol), 1-aryl-2-thiocyanatoethanone 2 (1 mmol) and Et3N (1mmol) in EtOAc (3 mL) was stirred at room temperature for 8 h. Then hydrazonoyl chloride 3 (1mmol) was added to the above mixture and the reaction was stirred at reflux temperature for 10min. After completion of the reaction, the reaction mixture was filtered, EtOAc was evaporated andthe residue was purified by recrystallization from ethanol to afford the pure product 4 in high yield.The two disterioisomers of products 4a-c were separated by washing the precipitate with n-Hexane/EtOAc (10/1)

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Article; Alizadeh, Abdolali; Moafi, Leila; Synlett; vol. 27; 12; (2016); p. 1828 – 1831;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 15861-23-1, name is Indoline-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H8N2

The 5 – cyano – indoline (1.00 g, 6. 94 mmol) and TEA (2.88 ml, 20.8 mmol) dissolved in DCM (30 ml) in, adding 3 – bromo – benzenesulfonyl chloride (1.95 g, 7.63 mmol) At room temperature overnight and for. Water quenching reaction, divide the DCM layer, for extracting the alternating layer twice twice DCM, the combined DCM layer turns on lathe does after drying, a yellow solid intermediate 1 a (2.26 g, yield: 90%) .

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Xiandao Pharmaceutical Development Co., Ltd.; Li Jin; Wang Wei; Chu Hongzhu; Lv Kaizhi; Liu Lichuan; Nong Yunhong; Chen Wei; (17 pag.)CN110256416; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H8ClNO2

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80 to 90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL ethanol. The solid was dissolved in 90 mL 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of isatin derivative (1.0 mmol), trans-4-hydroxy-L-proline (0.131 g,1 mmol), and CTAB (4 mmol) in water (50mL) was stirred at 80 C for 30 min. After completion of the reaction (monitored by TLC), the contents were filtered and the residue was washed thoroughly with water until free from CTAB. Finally, the residue was crystallized from a chloroform-petroleum ether mixture to afford the desired products in excellent yields. The characterizations of the products were accomplished by spectroscopic analysis (1H, 13C NMR, FTIR, and ESI-mass) and also by comparison of the data reported in the literature.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Naskar, Subhendu; Roy, Suprakash; Sarkar, Swarbhanu; Synthetic Communications; vol. 44; 11; (2014); p. 1629 – 1634;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem