Tag: M.W=100-200

141452-01-9, name is Methyl indoline-5-carboxylate, 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. SDS of cas: 141452-01-9

A 50 ml. RBF was charged with methyl, indoline-5-carboxylate, (2 g, 11 .3 mmol), DCM (20 ml_, 0.6 M), diisopropylethylamine (5.83 g, 45.1 mmol, 4.0 equiv.), and the stirred reaction mixture was then treated dropwise with benzyl chloroformate (5.78 g, 33.9 mmol, 3.0 equiv.). The reaction mixture was stirred for 24 h at RT and then concentrated under reduced pressure. The crude material was purified on silica gel (40 g Si02, 0-100% EtOAc-hexanes) to afford 0-1-benzyl-0-5-methylindoline-1 ,5- dicarboxylate (2.50 g, 3.52 theoretical, 71.0%). 1 H NMR (CDCI3): d 7.79-7.75 (m, 3H), 7.40-7.20 (m, 5H), 5.20 (s, 2H), 4.00 (t, 2H), 3.81 (s, 3H), 3.14 (t, 2H); LCMS: 312 (M+1 ).

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLLABORATIVE MEDICINAL DEVELOPMENT PTY. LTD.; WARNER, John, C.; BALDINO, Carmen; MUOLLO, Lauren; ROSENFELD, Craig; (109 pag.)WO2019/106434; (2019); A1;,
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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. 769965-95-9, name is 5′-Fluorospiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., Recommanded Product: 769965-95-9

A mixture of {5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl methanesulfonate (183 mg, 0.50 mmol), cesium carbonate (325 mg, 1.0 mmol) and 5′-fluorospiro[cyclopropane-1,3′-indol]-2′(1’H)-one (79 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL) was heated with stirring at 60C for 30 minutes. The resulting mixture was purified by preparative HPLC to afford the title product.

The synthetic route of 769965-95-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; GAO, Lu; GUO, Lei; HUANG, Mengwei; LIANG, Chungen; WANG, Baoxia; WANG, Lisha; WU, Guolong; YUN, Hongying; ZHANG, Weixing; ZHENG, Xiufang; ZHU, Wei; WO2014/184163; (2014); A1;,
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Related Products of 100510-65-4,Some common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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 A 6-Benzoylamino-2,3-dihydro-3,3-dimethyl-(1H)-indolin-2-one To a suspension of 5.28 g. (0.03 mole) 6-amino2,3-dihydro-3,3-dimethyl-(1H)-indolin-2-one and 4.6 ml. triethylamine in 50 ml. anhydrous dichloromethane is added dropwise at 0 C., within the course of 15 minutes, 4.36 g. (0.031 mole) benzoyl chloride, followed by stirring for 1 hour at ambient temperature. The reaction mixture is then mixed with 200 ml. ice water and the precipitate is filtered off with suction, washed with water and recrystallized from methanol. Yield 7.8 g. (93% of theory); m.p. 251-254 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Amino-3,3-dimethylindolin-2-one, its application will become more common.

Reference:
Patent; Boehringer Mannheim GmbH; US4985448; (1991); A;,
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Some common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-one, molecular formula is C8H8N2O, 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 5-Aminoisoindolin-1-one

Synthesis of 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) A mixture of 6-chloro-9H-purine (1, 0.15 g, 0.97 mmol), 5-aminoisoindoline-1-one (2, 0.14 g, 0.97 mmol) and (1S)-(+)-camphor-10-sulfonic acid (0.27 g, 1.16 mmol) in isopropanol (10 mL) was heated in a sealed tube at 100° C. for 4 h. After completion of the reaction, the mixture was concentrated. The obtained solid was filtered and re-crystallized from ethanol and isopropanol to afford 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) as off-white solid. Yield: 0.15 g, 58percent; MS (ESI) m/z 267 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 8.66 (s, 2H), 8.44 (s, 1H), 8.31 (d, J=1.9 Hz, 1H), 7.99 (dd, J=8.3, 1.8 Hz, 1H), 7.67 (d, J=8.3 Hz, 1H), 4.40 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 222036-66-0, its application will become more common.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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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., Application In Synthesis of 5-Methoxyisatin

General procedure: 30 mg of SiO2_g-C3N4 nanocomposite was dispersed in aqueous media (3 ml) for 30 min and dimedone or 4-hydroxycoumarin (1 mmol), malononitrile (1 mmol) and isatin (1.0 mmol) were added to the mixture. Then, the mixture was stirred at reflux conditions for an appropriate time, while the reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was employed for the extraction of crude product and the products were dried over anhydrous Na2SO4. The solvent was evaporated followed by recrystallizing of the crude product in hot ethanol, and pure products were identified by IR, 1H and 13C NMR spectral data. The SiO2_g-C3N4 nanocatalyst was washed with EtOH, dried and reused for the next run.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39755-95-8.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri, Mohammad Ali; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 1173 – 1188;,
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Application of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(1) Refer to Figure 2 to determine the microchannel reactor connection mode, remove the preheating zone module, the channel type is cylindrical straight channel and circular microchannel structure, the number of microchannel mixed reaction modules is determined according to the flow rate and residence time.The N-methylphthalimide-concentrated sulfuric acid solution was regarded as the raw material A, the concentrated nitric acid solution was regarded as the raw material B, and the two materials were injected into the reaction zone through the metering pump at a flow rate of 10 ml/min and 25 ml/min, respectively. In the mixed residence reaction, the molar ratio of concentrated nitric acid to substrate is 1.2:1, the mass ratio of substrate to concentrated sulfuric acid is 1:2, and the microchannel reactor of Fig. 2 is used to control the temperature of 60 C, residence time. 180s, the reaction solution was quantitatively collected, washed with ice water, washed with water, filtered, and dried to obtain N-methyl-4-nitrophthalimide nitrated product, HPLC content analysis (normalized) 97%, yield 96 %.

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-Methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Wanfeng Chemical Co., Ltd.; Liu Tao; Yao Chenhua; Yu Xingying; Yu Xiaotian; (11 pag.)CN109305933; (2019); A;,
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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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Oxoindoline-5-carboxylic Acid

To a stirred solution of 2-oxoindoline-5-carboxylic acid (0.7 g, 3.95 mmol) in DMF (5 mL) was added EDCI.HCl (1.13 g, 5.92 mmol), HOBt (0.8 g, 5.92 mmol) and triethylamine (1.7 mL, 11.8 mmol). The solution was stirred for 10 min at 0oC. After that tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (0.93 g, 4.34 mmol) was added and the reaction stirred at rt for 16 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4and concentrated under reduced pressure to obtain a crude residue which was purified by preparative HPLC to afford tert-butyl 4-((2-oxoindoline-5- carboxamido)methyl)piperidine-1-carboxylate (0.130 g, 8%)

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
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Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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. category: indolines-derivatives

Under argon atmosphere conditions, add 0.0133 g (0.10 mmol) of 2-methylindolinoline (1a), 0.0013 g (0.002 mmol) of acid eosin EosinY, 0.150 g of Antarctica lipase CAL-A, 0.0146 g (0.10 mmol) of n-octyl mercaptan, 0.104 g (0.50 mmol) of allyl-3-methoxyphenyl carbonate (2b), methyl tert-butyl ether (TBME) 2.0 mL;The reaction was stirred at 45 C for 6 hours under a 6w white light. After the reaction, the insoluble enzyme was removed by suction filtration, the solvent was distilled off under reduced pressure, and the solvent was separated by column chromatography. The eluent: (V) petroleum ether / (V) Ethyl acetate = 30/1. 0.0189 g of a yellow liquid product (3ab) was obtained with a product yield of 87%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6872-06-6, its application will become more common.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (16 pag.)CN110437123; (2019); A;,
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Synthetic Route of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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: To a 25 ml round bottom flask, a mixture of isatin / acenaphthoquinone / 2-hydroxynaphthoquinone/ ninhydrin (1 mmol), o-phenylene diamine (1 mmol) in ethanol (95 %, 10 mL) and sulfamic acid (20 mol %) was added. The reaction mixture was stirred at ambient temperature for time mentioned in Table II, monitored by TLC. After completion of reaction, the mixture was filtered washed with ethanol and dried to furnish the desired pure products in high yields.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hegade, Pravin G.; Mane, Mansing M.; Patil, Jayavant D.; Pore, Dattaprasad M.; Synthetic Communications; vol. 44; 23; (2014); p. 3384 – 3391;,
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Reference of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of magnesium (1.0 M in THF, 22 mL, 23.8 mmmol) was added 4-bromo-1-butene (2.2mL, 22 mmol) under a nitrogen atmosphere. After stirring the mixture for 30 min, the resultingsolution was added to the solution of N-methylphthalimide (1.42 g, 6.38 mmol) in THF (34 mL) at-20 C and stirred for additional 1 hour at the same temperature. The reaction was quenched byaddition of saturated aqueous NH4Cl (20 mL), and the resulting solution was extracted with EtOAc(30 mL). The organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered, andconcentrated in vacuo to give a crude material (1.61 g). To a solution of the crude material (1.61 g) in dichloromethane (68 mL) was added triethylsilane (4.3mL, 27 mmmol) and boron trifluoride diethyl ether complex (3.4 mL, 27 mmol) under a nitrogenatmosphere at -20 C. The mixture was allowed to warm to 0 C and stirred for 30 min. The reactionwas quenched by addition of saturated aqueous NaHCO3 (50 mL). The resulting solution wasextracted with EtOAc (60 mL). The organic extracts were washed with brine (50 mL), dried overNa2SO4, filtered, and concentrated in vacuo to give a crude material. This material was purified bycolumn chromatography (silica gel, hexane/EtOAc = 3/1 to 1/1) to give 3a (1.17 g, 5.81 mmol, 85%for 2 steps) as a pale yellow oil. Rf = 0.32 (silica gel, hexane/EtOAc = 1/1); 1H NMR (300 MHz, CDCl3) delta 7.83 (d, J = 6.6 Hz, 1H, ArH), 7.56-7.41 (m, 3H, ArH), 5.70 (ddt, J = 6.3, 10.5, 17.1 Hz, 1H, CH),4.97-4.90 (m, 2H, CH2), 4.53 (t, J = 4.2 Hz, 1H, CH), 3.11 (s, 3H, CH3), 2.13-2.00 (m, 2H, CH2), 1.80 (m, 1H,CH2), 1.60 (m, 2H, CH2); 13C NMR (75 MHz, CDCl3) delta 168.5 (C), 144.6 (C), 137.1 (CH), 132.7 (C),131.2 (CH), 128.0 (CH), 123.4 (CH), 121.9 (CH), 115.1 (CH2), 60.9 (CH), 29.7 (CH2), 27.2 (CH3),26.6 (CH2).

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

Reference:
Article; Sengoku, Tetsuya; Nagai, Yuichiro; Inuzuka, Toshiyasu; Yoda, Hidemi; Synlett; vol. 30; 2; (2019); p. 199 – 202;,
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