Category: indolines-derivatives

Synthetic Route of 15861-23-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15861-23-1 name is Indoline-5-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The 5 – cyano – indoline (0.14 g, 1. 00 mmol) is added to dichloromethane (6 ml) in, adding pyridine (0.24 g, 3. 00 mmol) and intermediate 6 a (0.27 g, 1.000 mmol), Canada finishes after stirring at room temperature 1 hour. Concentrated under reduced pressure the crude intermediate 6 b directly used for the next step reaction.

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

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

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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Methoxyisatin

General procedure: A mixture of isatin derivatves (1 mmole), malononitrile (1 mmole),1,3-dicarbonyl compounds (1 mmole), and Fe3+-mont. (0.05 g) in CH3CN(5 mL) was heated using an Elmasonic S 40 H ultrasonic cleaning unit at 50 C under silent condition. The progress of the reaction was monitored by TLC (EtOAc/hexane 3:7). After completion of the reaction, the catalyst was removed by filtration. Water was added to the residue. The solid which was obtained was filtered off and dried to provide pure products of the spirooxindole derivatives (4a-j) (Table 3).

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Pourshiva, Mina; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 39; 6; (2015); p. 314 – 317;,
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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Product Details of 7477-63-6

General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.

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; Shang, Jian-Li; Guo, Hui; Li, Zai-Shun; Ren, Biao; Li, Zheng-Ming; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 724 – 727;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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 2; The mixture of methylene chloride (130 ml) and 1-(1,2-Benzisothiazol-3- yl)piperazine (9.5 gm) is stirred for 10 minutes, triethylamine (17 ml) is added drop wise for 15 minutes at 25 – 300C and then tetrabutyl ammonium bromide (4 gm) is added. Then trimethylsilyl chloride (9.5 ml) is added to the contents drop EPO wise for 20 minutes and stirred for 1 hour. The reaction mass is heated to 400C and methylene chloride is distilled off under vacuum. Then the reaction mass is cooled to 300C, dimethylformamide (75 ml) is added and stirred for 15 minutes. The reaction mass is filtered on hi-flo and washed with 50 ml of dimethyl formamide.The mixture of 5-(2-Chloroethyl)-6-chloro-oxindole (10 gm), water (25 ml), dimethyl formamide (35 ml) and sodium carbonate (10 gm) is heated to 1100C and to this mixture, above filtrate is slowly added drop wise at same temperature for 30 minutes. Then the reaction mass is stirred until completion of the reaction and then cooled to 300C. The reaction mass is added to chilled water (500 ml) and stirred for 20 minutes. The solid is filtered, slurried in isopropyl alcohol (200 ml). Then the solid is filtered, washed with isopropyl alcohol (100 ml), the solid is again slurried in isopropyl alcohol at reflux and refluxed for 1 hour. Then resulting solid is filtered at reflux point and washed with isopropyl alcohol (60 ml) to give 10 gm of ziprasidone (HPLC purity: 99.05%)..

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HETERO DRUGS LIMITED; WO2006/80025; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 appropriate oxindole (7a-e, 0.3 mmol) in ethanol (3 mL) was added corresponding aldehydes (11a-e,0.32 mmol) and a catalytic amount of piperidine. The reaction mixture was stirred at reflux for 6-12 h (reaction monitored byTLC). After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones title compounds of formula (4a-v) as yellow/brown/orange solids in moderate to excellent yields.

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Naidu; Srinivasulu, Gannoju; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 34 – 46;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

Example 58B 2-(3-hydroxy-3-phenylcyclopentyl)isoindoline-1,3-dione A solution of Example 58A (1.00 g, 4.36 mmol) and THF (20 mL) was cooled to <-70 C. and phenylmagnesium chloride (2.40 mL, 4.80 mmol) was added at <-70 C. After 2 hours, saturated aqueous NH4Cl (20 mL) was added and the mixture was extracted with MTBE (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was puridifed by flash column chromatography (0-20% EtOAc/hexanes, gradient elution), to provide the title compound (370 mg, 1.20 mmol, 27.6% yield). The synthetic route of 1029691-06-2 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ABBOTT LABORATORIES; US2012/245163; (2012); 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 132898-96-5 as follows. COA of Formula: C8H4ClNO4S

General procedure: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

According to the analysis of related databases, 132898-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1914-02-9, name is 3,3-Dimethylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3,3-Dimethylindoline

EXAMPLE 1 N-(3,3-Dimethylindolin-1-yl)-3-(4-imidazolyl)propionamide monohydrochloride (E1) STR9 A suspension of 3-(4-imidazolyl)propionic acid monohydrochloride (2.0 g) (Chem. Ber. 66, 156 [1933]) in thionyl chloride (10 ml) and DMF (3 drops) was stirred at room temperature for 3 h. The excess thionyl chloride was removed by rotary evaporation and the residue re-evaporated with 2*50 ml of dry toluene. The residue was suspended in CH2 Cl2 (100 ml) and a solution of 3,3-dimethyl indoline (1.7 g) and triethylamine (4 ml) in CH2 Cl2 (50 ml) was added with stirring and cooling. The reaction mixture was stirred overnight, washed with saturated NaHCO3 and the lower organic layer dried (Na2 SO4). Concentration of the organic extracts afforded the crude product which was purified by column chromatography on silica, eluding with CHCl3 containing increasing quantities of methanol.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beecham Group p.l.c.; US4918079; (1990); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5428-09-1, name is 2-Allylisoindoline-1,3-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 5428-09-1, SDS of cas: 5428-09-1

To a solution of 2-allylisoindoline-1,3-dione 11(13.0 g, 69.4 mmol) in CH2CI2 (500 mL) was added AIIyITMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 ¡ãC and stirred under reflux for 4 h.Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCI solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (3 x 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removedunder reduced pressure. Column chromatography over SiC2 (Cyclohexane/ EtOAc =85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 percent) as a yellow resin.R: 0.57 (Cyclohexane/EtOAc = 85:15)1H NMR (300 MHz, CDCI3) 6 = -0.10?0.09 (m, 9H), 1.44 (d, J = 8.2 Hz, 1.6 H), 1.72(d, J= 8.8 Hz, 0.4 H), 4.21 (d, J= 6.5 Hz, 1.6 H), 4.29 (dd, J= 14.5, 5.9 Hz, 0.4 H),5.26 ? 5.47 (m, 0.8 H), 5.56 ? 5.70 (m, 0.2 H), 5.70 ? 5.87 (m, 0.8 H), 5.94 ? 6.09 (m,0.2 H), 7.65 ? 7.74 (m, 2H), 7.79 ? 7.88 (m, 2H).?3C NMR (75 MHz, cdcl3) 6 = -2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51,121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Allylisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

6-Nitroindoline (5 g) was dissolved in 200 mL ofdichloroethane. N-Methyl-4-piperidone (5 g) was added to themixture, followed by NaHB(OAc)3 (12 g) and 1 mL of glacialAcOH. The mixture was stirred at RT overnight. A saturatedNaHC03 (200 mL) solution was added to the reaction mixtureand stirred for 1 h. The resulting mixture was separated byseparation funnel. The organic layer was extracted once withsaturated NaHC03 solution and once with brine. The resultingorganic layer was dried over MgS04, filtered andconcentrated in vacuo. The crude material was purified byflash chromatography on silica gel with 2:1 EtOAc:MeOH toafford orange oil. MS: 262 (M+l) . Calc’d. for C14H19N302 -261.3.

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

Reference:
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem