Author: Jessica.F

These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-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. Computed Properties of C9H6ClNO2

The N,Se acetal 5 was prepared by a slight and safer modification of the original procedure4 where, the required phenylselenol intermediate was replaced by sodium phenylselenolate. In a 50 mL three-neck flask equipped with a reflux condenser were placed diphenyl diselenide (0.63 g, 2 mmol) and 16 mL of dry DMF. The solution was heated at 60 C and stirred rapidly under nitrogen while NaBH4 (0.15 g, 4 mmol) was added portionwise. Hydrogen was evolved and the reaction mixture turned colorless and homogeneous upon complete reduction of the selenide. The reaction was heated at 110 C for 1 h and then cooled to room temperature. Solid N-chloromethylphthalimide (0.78 g, 4 mmol) was added to the orange solution. After stirring at room temperature for 12 h, 2 N aqueous hydrochloric acid (10 mL) was added carefully to the white suspension. The entire product mixture was poured into 50 mL of water and 40 mL of diethyl ether, mixed, and separated. The aqueous phase was extracted with 20 mL of diethyl ether and the combined organic phases were washed with H2O (4 ¡Á 10 mL), 10 mL of brine, dried over sodium sulfate and concentrated. The solid residue was washed with light petroleum (2 ¡Á 10 mL) and dried over P2O5 to afford 5 in 82% yield and with spectral data in good agreement with those reported in the literature.4

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Temperini, Andrea; Minuti, Lucio; Tetrahedron Letters; vol. 53; 22; (2012); p. 2709 – 2711;,
Indoline – Wikipedia,
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Electric Literature of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32692-19-6, Recommanded Product: 32692-19-6

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 885272-46-8

A solution of tert-butyl 4-bromoindoline-1-carboxylate (0.50g),bis(triphenylphosphine)palladium(II) dichioride (0.24 g), copper iodide (64 mg),triphenyiphosphine (0.18 g), hexamethyldisilazane (0.52 mL) and triethylamine (1.7 g) in DMF (8.4 mL) was evacuated and backfilied with nitrogen three times. The mixture was stirred for 10 minutes at 110 C. 2-[2-(4-Ethynylphenoxy)ethoxyjtetrahydropyran (0.83 g) was added into the mixture. The reaction mixture was stirred for 5 hours at 110 C and overnight at room temperature, quenched with water and extracted with EtOAc. The organiclayer was washed with water twice, dried over MgSO4, filtered and concentrated in vacuo. The residue was charged onto ISOLUTE HM-N and purified with OH-type silica gel column chromatography (3-100 % EtOAc in n-hexane) to give the title compound (0.57 g, 73 % yield) as a colorless solid.?H NMR (600 MHz, CHLOROFORM-d)6 ppm 1.50- 1.67(m, 13 H), 1.71 – 1.79(m, I H),1.81 – 1.89 (m, I H), 3.18 -3.25 (m, 2 H), 3.51 -3.57 (m,1H), 3.80-3.86 (m, I H), 3.87-3.93 (m, 1 H), 3.96 – 4.10 (m, 3 H), 4.13 – 4.23 (m, 2 H), 4.68 – 4.74 (m, 1 H), 6.89 – 6.94 (m,2 H), 7.05 – 7.17 (m, 2 H), 7.26 – 7.27 (m, 1 H), 7.40 – 7.48 (m, 2 H).

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; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; USHIYAMA, Fumihito; YAMADA, Yousuke; MATSUDA, Yohei; YOSHIZUMI, Takashi; KIM, Chunhae; YAMAGISHI, Junya; ARRATE, Alba Teresa Macias; ROUGHLEY, Stephen David; McKENNA, Sean; WALMSLEY, David Lee; (108 pag.)WO2018/216823; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 39603-24-2, Recommanded Product: 39603-24-2

General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Dandia, Anshu; Khan, Shahnawaz; Soni, Pragya; Indora, Aayushi; Mahawar, Dinesh Kumar; Pandya, Prateek; Chauhan, Chetan Singh; Bioorganic and Medicinal Chemistry Letters; vol. 27; 13; (2017); p. 2873 – 2880;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 239463-85-5, A common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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: 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H-indol-1-yl}Propyl benzoate(2R, 3R) -mono-tartaric acid salt(Mono-tartaric acid salt of the compound of formula (II)),Potassium carbonate (80 g),And a mixed solvent of acetonitrile and dimethylacetamide (ACN / DMAC = 500 mL / 500 mL) was heated to 80 DEG C,Stir for 30 min. To the reaction mixture were added 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula 3) and 9.70 g of KI,The reaction was carried out at the same temperature for 10 hours.The reaction mixture was cooled to room temperature,And extracted with 1 L of ethyl acetate and 1.5 L of water.The organic layer obtained by layer separation was washed with 1 L of brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing again with 200 mL of ethyl acetate, the solvent was removed by distillation. 400 mL of methanol, 100 mL of water and 20 g of KOH were added to the obtained residue. After the mixture was stirred at room temperature for 10 hours,1 L of ethyl acetate and 1 L of water were added and extracted for 10 minutes.The organic layer obtained by layer separation was washed sequentially with 1 L of saturated aqueous solution and 1 L of saturated brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing with 200 mL of ethyl acetate,18 g of oxalic acid was added.The reaction mixture was stirred at 50 for 30 minutes, It cooled to room temperature.600 mL of isopropyl ether was added to the reaction mixture,Stirred for 2 hours, and then filtered.The obtained crystals were washed with 200 mL of isopropyl ether,At 40 for 10 hours to give the titled compound as a dried in vacuo to 88 g.The reaction was carried out in the same manner as in Example 1, except that 23.5 g of fumaric acid was used instead of oxalic acid to obtain 92 g of the title compound.Yield: 81%Purity: 99.5%Impurities (dimer): Not more than 0.1%

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; Dasan Medichem Co., Ltd.; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Kim, Jae Hyung; Aum, Woon Yong; (12 pag.)KR2016/92976; (2016); 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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C9H6ClNO2

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

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; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, These common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, 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.

EXAMPLE 308; 3-(6-Chloro-2-propyl-2H-pyrazolo[3,4-d]pyrimidin-4-yl)-5-methyl-1,3-dihydroindol-2-one; A solution of 5-methyloxindole (147 mg, 1.0 mmol) and compound 105 (231 mg, 1.0 mmol) in 2 mL dry THF and 2 mL dry DMF was cooled to 0 C., and a dispersion of 60% NaH in mineral oil (80 mg, 2.0 mmol) was added. After the hydrogen evolution ceased, the reaction mixture was allowed to warm to rt. The reaction mixture was stirred under N2 for 2 days. The dark yellow homogeneous reaction was quenched with sat. NH4Cl, and a yellow precipitate formed. The precipitate was washed with water, and the product allowed to air dry. The crude product was then suspended in diethyl ether, and the yellow solid recovered by filtration affording g (80%) of the product: mp 275-80 C. 1H NMR (400 MHz, TFA-d): delta 9.68 (s, 1H), 8.41 (br s, 1H), 8.09 (d, J=7.8 Hz, 1H), 8.02(d, J=7.8 Hz, 1H), 5.33(q, J=6.3 Hz, 2 H), 3.30 (s, 3H), 2.97(dq, J=6.3,7.1 Hz), 1.93(t, J=7.1 Hz).

Statistics shows that 5-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 3484-35-3.

Reference:
Patent; Cephalon, Inc.; US2007/281949; (2007); A1;,
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 19727-83-4 as follows. Application In Synthesis of 6-Nitroindoline

Reference Example 58 In 50 ml of methylene chloride was dissolved 2.5 g of 6-nitroindoline, and then 6.37 ml of triethylamine was added thereto. Under ice cooling, 3.51 g of methanesulfonyl chloride was added dropwise, the reaction solution was stirred at room temperature for 3 hours, and then ice-water was added thereto, followed by 1 hour of stirring. The reaction solvent was removed by evaporation under reduced pressure, a 1M aqueous hydrochloric acid solution was added to the residue, and precipitated was filtrated off, whereby 3.52 g of 1-methylsulfonyl-6-nitroindoline was obtained as a brown solid.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; EP1632477; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem