Category: indolines-derivatives

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. 550-44-7, name is 2-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Methylisoindoline-1,3-dione

Add a nitrating agent to N-methylphthalimide at -5 C, and react at 40 C for 4h, then extract with an extraction solvent dry,N-methyl-4-nitrophthalimide is formed.The extraction solvent is ethyl acetate and dichloromethane, and the weight ratio is 1: 0.6. The weight ratio of the extraction solvent and N-methylphthalimide is 1: 1.

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 550-44-7.

Reference:
Patent; Shandong Juancheng Fangyuan Bearing Chemical Co., Ltd.; Li Zhi; Zhang Hongyuan; Zhang Heji; (13 pag.)CN110437131; (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., Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

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 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; 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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Synthetic Route of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows.

Step 2. fert-Butyl-5-bromoindoline-l-carboxylate (BI12): To a stirred solution of 5- bromo-indoline (3.0 g , 15mmol) in acetonitrile (100 ml), was added DMAP (0.185 g , 1.522 mmol) and di-ieri-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2X). The combined ether layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

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

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); A1;,
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Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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. COA of Formula: C14H13NO3

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
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Application of 141452-01-9, A common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

Reference Example 15 methyl 1-(6-chloropyrimidin-4-yl)-2,3-dihydro-1H-indole-5-carboxylate; A mixture of methyl 2,3-dihydro-1H-indole-5-carboxylate (5.19 g), 4,6-dichloropyrimidine (4.37 g), and ethanol (50 mL) was stirred overnight with heating under reflux, and concentrated under reduced pressure. To the residue were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the mixture was stirred for 30 min. Insoluble materials were collected by filtration to give the title compound (5.87 g, 69%) as a white solid. 1H-NMR (300 MHz, CDCl3)delta:3.32 (t, J=8.7 Hz, 2 H), 3.91 (s, 3 H), 4.08 (t, J=8.7 Hz, 2 H), 6. 66 (s, 1 H), 7.90 (s, 1 H), 7.95 (d, J=8.5 Hz, 1 H), 8.46 (d, J=8.5 Hz, 1 H), 8.64 (s, 1 H).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
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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. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

To a stirred solution of 200 mg (0.87 mmol) of 2-(3-oxocyclopentyl)isoindoline-1,3-dione (CAS 1029691-06-2) in 5 mL of DCM at 0C were added 10mg (0.26 mmol) of NaBH4 and then lmL of MeOH. Themixture was stirred at this temperature for 0.5 h. 20 mL of H20 was added and the mixture was extractedwith DCM. The combined organic layers were dried over Na2SO4 and then concentrated under vacuum. The residue was purified by silica gel column chromatography (PE/ EA = 2/1) to give 96 mg of the product as a white solid.MS (ESI+): 232.0 [M+H].?H NMR (400 MHz, DMSO-d6) ppm: 7.76-7.83 (m, 5H), 4.80 (d, J = 5.2 Hz, 1H), 4.43 (m, 1H), 4.06 (m, 1H), 1.64-2.15 (m, 6H).

The synthetic route of 1029691-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; POHLMANN, Jens; STIEGER, Martin; REINELT, Stefan; LANE, Heidi; (286 pag.)WO2016/128465; (2016); A1;,
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Electric Literature of 18711-15-4, A common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, molecular formula is C8H3Cl2NO2, 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.

2.25 g of magnesium for a Grignard reaction in 15 ml of anhydrous THF are placed in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen. A mixture of 13.6 g of 5-bromobenzofuran in 35 ml of anhydrous THF is then added. The mixture is stirred for one hour, followed by addition of a solution of 5 g of 4,6-dichloro-1H-indole-2,3-dione in 50 ml of anhydrous THF. The mixture is stirred at room temperature for 4 hours 30 minutes. Water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is separated out, dried over Na2SO4, filtered and evaporated under vacuum. The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The solid is taken up in ethyl ether and filtered off. 4.2 g of expected product are obtained. TLC: 6/4 hexane/EtOAc, Rf=0.35

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; SANOFI; US2012/40996; (2012); A1;,
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These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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 C8H4ClNO2

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 °C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
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Some common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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. Product Details of 324-03-8

General procedure: Target compounds 3 were prepared by coupling compounds 1 or 2 with hydrazine hydrate under a mild condition. A mixture of isatin or an N1-substituted isatin (10 mmol) and hydrazine hydrate (5 mmol) was refluxed in ethanol (50 mL) in the presence of acetic acid as the catalyst for 0.5-2 h. After completion of the reaction (monitored by TLC), the solvent was removed under reduced pressure and the crude product was washed with water and recrystallized from ethanol to give pure products (Table 1). Some compounds synthesized in the current study are known compounds and their physicochemical characteristics are consistent with those reported in earlier literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 324-03-8, its application will become more common.

Reference:
Article; Liang, Chengyuan; Xia, Juan; Lei, Dong; Li, Xiang; Yao, Qizheng; Gao, Jing; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 742 – 750;,
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Electric Literature of 4403-36-5, The chemical industry reduces the impact on the environment during synthesis 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, I believe this compound will play a more active role in future production and life.

To 3-exo-[(S)-1-((S)-2-methyl-propane-2-sulfinylamino)-2-(2,4,5-trifluoro-phenyl)-ethyl]-8-aza- bicyclo[3.2.1]octane (540 mg, 1.2 mmol) in dichloromethane/1 M NaOH (1/1, 5 mL) is added 2-phthalimidoethane sulfonyl chloride (1.101 g, 3.59 mmol) then the resulting mixture is stirred at 500C during 16h. It is extracted with dichloromethane, the organic phase is dried and evaporated to give a white solid. MS: 626 [M+H]+HPLC (Zorbax SB C18, 2min method (0-0.8min 10-95%ACN, 0.8-1.5min 95%ACN, 1.5- 1.6min 95-10%ACN, 1.6-2min 10%ACN): 1.44 min.

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-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/115821; (2007); A2;,
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