Author: Jessica.F

201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-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. Application In Synthesis of tert-Butyl 5-bromoisoindoline-2-carboxylate

5-Bromo-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (2.97 g, 10 mmol) was azeotropically dried by evaporation from toluene. Tris(dibenzylideneacetone)dipalladium (0) (228 mg, 0.25 mmol), 2-(di-tert-butylphosphino)biphenyl (149 mg, 0.50 mmol) and sodium tert-butoxide (1.34 g, 13.9 mmol) were added and the flask was purged with nitrogen. Toluene (25 ml.) then N-methylpiperazine (1.33 mL, 12 mmol) were added and the mixture was heated to 8O0C for 2 hours. After allowing to cool to r.t. the mixture was diluted with ether, filtered through Celite and concentrated to give a residue that was purified by flash chromatography on silica (2M methanolic ammonia/dichloromethane, 1% to 3% gradient). This afforded the title compound as a brown solid (1.45g, 46%). 1H NMR (MeOH-d4) 7.15 (1H, m), 6.94-6.88 (2H, m), 4.60-4.54 (4H1 m), 3.20-3.17 (4H, m), 2.63-2.60 (4H, m), 2.34 (3H, s), 1.52 (9H, s). MS: [M+H]+ 318.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
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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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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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C22H19N3O6

Add 4 kg of N,N-dimethylacetamide to a 10 L reaction flask.Add 1.0 kg of compound (II), add 1.4 kg of ethylenediamine, stir and heat.The reaction was stirred at 40 C for 4 h. The reaction solution was cooled to 30 ± 5 C,Add about 1.2kg of phosphoric acid, add the reaction, and cool the reaction solution to 10±5C for 1h~1.5h.Filtration, filter cake washed with N, N-dimethylacetamide, ethanol,The wet product was transferred to a blast oven, and the internal temperature of the oven was controlled to dry at 50-55 C for 16 ± 1 hour to obtain a white solid. Yield: 93%, product purity (HPLC): 99.5%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changzhou Pharmaceutical Factory Co., Ltd.; Guo Yijie; Jin Xiaofeng; Shao Zhichun; (13 pag.)CN110156768; (2019); A;,
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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. 337536-15-9, name is 4-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6BrNO

A suspension of Example 1C (2g, 9.43 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxa-borolan-2-yl)aniline (2.5g, 11.3 mmol), and Na2CO3 (2.2g, 20.8 mmol) in DME (68 mL) andwater (17 mL) was purged with nitrogen, treated with Pd(PPh3)4 (Ig, 0.9 mmol), and stirredat 90 C for 19 hours. The reaction mixture was cooled to room temperature, concentrated toone-third its original volume, diluted with ethyl acetate (30 mL) and water (20 mL), andfiltered. The filter cake was washed with water and ethyl acetate and dried to give 1.25g ofthe desired product.

According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/108672; (2004); A1;,
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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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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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C21H21N3O5

100 g (R)-2-(2-hydroxy-3-(4-(3-oxo-morpholino) phenyl amino) propyl) isoindoline-i ,3-dione of Formula (F) and MDC (i000 ml) were added to REF at 25 C. to 35 C. and heated to 40 C. to 45 C. Further, 6i g N,N-Carbonyl diimidazole (CDI) and 0.5 g DMAP were added and stirred for 3-4 hours. Excess MDC was evaporated under, reduced pressure. The reaction mass was cooled to 25 C. to 35 C. followed by addition of dilute HC1 solution and stirred for i hour and finally filtered and washed with 2×200 ml water to afford title compound as (S)-2-((2-oxo-3-(4-(3-oxo-mor- pholino)phenyl)oxazolidin-5-yl)methyl)isoindoline- i ,3-di- one of Formula (I).Excess MDC was evaporated under, reduced pressure. The reaction mass was cooled to 25 C. to 35 C. followed by addition of dilute HCl solution and stirred for 1 hour and finally filtered and washed with 2*200 ml water to afford title compound as (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione of Formula (I).

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 446292-07-5.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); 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. 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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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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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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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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