Tag: M.W=200-300

Reference of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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 solution of 4,7-dichloroisatin (0.68 mmol, 1.0 eq) in DMF (4 mL) was added K2CO3 (0.68 mmol, 1.0 eq) at room temperature, the mixture was stirred for about 30 min, and then the propargyl bromide (0.75 mmol, 1.1 eq) was added dropwise. The mixture was stirred overnight at room temperature. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc for several times; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Compound 2, saffron solid, yield: 76%, m. p.: 151.8-153.3 C, Rf = 0.52 (petroleum ether/ethyl acetate 2/1). 1H NMR (400 MHz, CDCl3) delta 7.51 (d, J = 8.7 Hz, 1H), 7.10 (d, J = 8.7 Hz, 1H), 4.94 (d, J = 2.4 Hz, 2H), 2.34 (t, J = 2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 178.68, 157.00, 146.19, 140.48, 133.05, 126.79, 117.16, 116.11, 77.22, 73.27, 31.94.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Yu, Bin; Wang, Sai-Qi; Qi, Ping-Ping; Yang, Dong-Xiao; Tang, Kai; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 350 – 360;,
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These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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 C8H4BrNO2

4-bromoisatin 1.0g (4.4mmol), methyl acrylate 0.46g (5.3mmol), PdCl2(PPh3)2 0.15g (0.22mmol), K3PO4 1.6g (6.2mmol). Place into microwave reaction flask. Add 5 ml DMF. Place under argon protection. In the microwave reactor 145 °C reaction 30min. TLC detection after the reaction is complete, the reaction solution with 100 ml saturated salt water washing 3 times, dichloromethane is used for extraction, the combined organic phase, anhydrous sodium sulfate drying, developing agent for petroleum ether: ethyl acetate=5:1 – 1: 1,200 – 300 mesh silica gel column chromatography purification, be 4 – acrylic acid methyl ester indole dione 0.65g, yield 64percent.

The synthetic route of 4-Bromoisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (8 pag.)CN104387312; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, name: 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
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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 2436-29-5 as follows. COA of Formula: C11H9NO3

Step 11. 2-(3-{[1-(3-Benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione; The product from Step 10 (20), 42 mg (0.13 mmol) was dissolved in anhydrous CH2Cl2 followed by the addition of phthalimide protected 3-aminopropionaldehyde 33 mg (0.16 mmol) and 37 mg (0.18 mmol) of sodium acetoxyborohydride and finally 10 mul (0.18 mmol) of acetic acid. The reaction was left stirring at room temperature for 2.5 h. The solvent was evaporated and the product redissolved in ethyl acetate and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated and dried under high vacuum resulting in 63 mg (0.13 mmol, 94%) of 2-(3-{[1-(3-benzyl-4-oxo-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (21) as a white solid.

According to the analysis of related databases, 2436-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiron Corporation; US2005/228002; (2005); A1;,
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Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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. Safety of 2,3-Dioxoindoline-5-sulfonyl chloride

A solution of rpml21 (0.211 g, 0.861 mmol) and morpholine (0.187 g, 2.139 mmol, 2.5 eq), in anhydrous DCM (7 ml) and anhydrous chloroform (1 ml) was stirred for 3h at room temperature under Ar. The yellow precipitate was collected by filtration and dried under vacuum. The crude product was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 132898-96-5, its application will become more common.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; WO2007/117699; (2007); A2;,
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Application of 320734-35-8,Some common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, molecular formula is C8H6BrNO, 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 2a-j (1.50 mmol) and 5 (1.50 mmol) in ethanol (10 mL) was treated with a catalytic amount of piperidine. The reaction mixture was stirred under reflux until complete consumption of the substituted indolin-2-ones was observed by TLC. After cooling, the precipitate was filtered, recrystallised from absolute ethanol and dried in air to furnish pure (E)-3-(benzothiazol-2-ylmethylene)indolin-2-ones 6a-j.

The synthetic route of 320734-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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Electric Literature of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 9 1-(2,6-Dichlorophenyl)-3-isopropylidene-1,3-di-hydro-2H-indol-2-one 1-(2,6-Dichlorophenyl)-oxindole (27.8 g; 0.10 mole) is dissolved in 300 ml of acetone, pyrrolidine (10 ml; 0.12 mole) is measured to the solution and it is warmed to reflux temperature. The reaction mixture is refluxed for 3 hours and the solution is evaporated. The product separated in crystalline form is dissolved in dichloro-methane, extracted twice with 10% hydrogen chloride, the organic phase is dried over sodium sulfate, clarified with bone coal, filtered and evaporated. The product is used for the catalytic hydrogenation without recrystallization. Analytical samples may be obtained by recrystal-lization from ethyl acetate. Yield: 31.82 g of yellow crystal (97%). M.p.: 180-182 C. (ethyl acetate). IR (KBr): 1700 (C=O), 793 cm-1. 1H-NMR (CDCl3, TMS, 400 MHz): 2.46 (3H, s), 2.66 (3H, s), 6.40 (1H, dd, J=0.6, 7.8 Hz), 7.09 (1H, dt, J=1.2, 7.6 Hz), 7.17 (1H, dt, J=1.0, 7.6 Hz), 7.35 (1H, dd, J=7.6, 8.7 Hz), 7.50 (2H, d, J=8.2 Hz), 7.64 (1H, d, J=7.5 Hz) ppm. 13C-NMR (CDCl3, TMS, 101 MHz): 23.4, 25.4, 108.5, 122.0, 122.3, 123.7, 123.8, 127.6, 128.9, 130.4, 130.9, 135.9, 140.0, 156.1, 166.2 ppm. Analysis for the Formula C17H13Cl2NO (318.21): Calculated: C, 64.17; H, 4.12; Cl, 22.28; N, 4.40%. Found: C, 64.02; H, 4.11; Cl, 22.14; N, 4.39%.

The synthetic route of 1-(2,6-Dichlorophenyl)-2-indolinone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EGIS GYOGYSZERGYAR RT.; US2007/232619; (2007); A1;,
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Reference of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 solution of chromones 1 (0.2 mmol), isatins 2 (0.3 mmol) and proline, or thioproline (0.5 mmol) in the 4.0 mL of EtOH at 80 C in oil bath for 3 h. After completion of the reaction, as indicated by TLC, the reaction solvent was directly removed, and purification by flash column chromatography (petroleum ether/EtOAc = 5:1~10:1) was carried out to furnish the corresponding products 3.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yue, Jing; Chen, Shuang; Zuo, Xiong; Liu, Xiong-Li; Xu, Sheng-Wen; Zhou, Ying; Tetrahedron Letters; vol. 60; 2; (2019); p. 137 – 141;,
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Application of 959235-95-1, The chemical industry reduces the impact on the environment during synthesis 959235-95-1, name is 6-(Trifluoromethoxy)indoline, I believe this compound will play a more active role in future production and life.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (577 mg, 2.84 mmol),2-(2-(4-(tert-butoxy)-4-oxobutoxy)-4-ch lorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 7d (1 .5 g, 2.84 mmol), HATU (1 .62 g, 4.26 mmol) and diisopropylethylamine (1 .4 mL, 8.5 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken upwith EtOAc, washed with an aqueous solution of K2003 10%, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 120 g, heptane/EtOAc 60/40) to give, after crystallization from petroleum ether/diisopropyl ether, tert-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(methylsulfonyl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)butanoate 9a (1 .02 g).

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, 6-(Trifluoromethoxy)indoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
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Synthetic Route of 667463-64-1,Some common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

I-3.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C. for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003.

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
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