Tag: M.W=100-200

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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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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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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

Commercially available 4-aminophthalimide (500 mg, 3.08 mmol) was dissolved in acetonitrile (15 mL). To the mixture were added cesium iodide (961 mg, 3.70 mmol), iodine (947 mg, 3.70 mmol), and copper iodide (712 mg, 3.70 mmol) at room temperature, and then an 11% aqueous hydrogen iodide solution (15 mL) and isoamyl nitrite (1.24 mL, 9.24 mmol) at 0C. The mixture was stirred at room temperature for 6.5 hours, and then for 1.5 hours after adding isoamyl nitrite (4.96 mL, 37.0 mmol). Then, saturated sodium bicarbonate was added to the mixture, and after filtration through sellite, the organic layer was separated. The resulting organic layer was washed with a saturated aqueous sodium thiosulfate solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was triturated with chloroform, and the resulting solid was filtered off and dried to give 4-iodophthalimido (394 mg, 47%). ESI-MS: m/z 272 [M-H]-.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
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Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

[0521] The 5-CHLORO-7-METHYL-LH-INDOLE-2, 3-dione (25.0 g, 0.13 mol), potassium hydroxide (8.4 g, 0.15 mmol) and 30% hydrogen peroxide (21.6 g, 0.18 mol) were mixed together in methanol (300 mL) at 0C for 2 h followed by 16 h at room temperature. The solution was poured into ethyl acetate (500 mL) and extracted with 1 N hydrochloric acid (3 x 200 mL) followed by brine (1 x 50 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The 2-amino-5-chloro-3-methylbenzoic acid (18.0 g, 0.10 mmol) was isolated as a yellow solid (75% yield). HRMS 7NEZ 185.0238 ; calcd 185.0244.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-7-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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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. 1504-06-9, name is 3-Methyloxindole, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Methyloxindole

General procedure: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

According to the analysis of related databases, 1504-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Methylindolin-2-one

General procedure: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

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 3484-35-3.

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
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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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6N2O3

5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of 5-amino-2-oxindole as a white solid.

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; SUGEN, Inc.; US2002/183364; (2002); A1;,
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Reference of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

6-Aminoindoline A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1 H NMR (400 MHz, CDCl3) 7.40 (d, J=7.4, 1H), 6.05 (d, J=2.0, 1H), 6.03 (d, J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t, J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t, J=8.2, 2H).

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; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Indoline – Wikipedia,
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Synthetic Route of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

A mixture of the appropriate amine (1 mmol) and the appropriate benzyl bromide (1 mmol) in DMF (0.5 M) was stirred at room temperature up to 100 C until completion of the reaction (up to5 days). The reaction mixture was either diluted with EtOAc and the resultant precipitate filtered to give pure product or quenched with sat. NaHCO3 and extracted with EtOAc. Crude material was purified either by automated flash chromatography (EtOAc:hexanes mixture) or by preparative HPLC to give the desired compound in 10-50% yield; ?H NIVIR (400 MHz, DMSO-d6)10.80 (s, 1H), 7.55 (dd, J= 13.2, 8.2 Hz, 3H), 7.48 – 7.40 (m, 1H), 7.15 (t, J 4.7 Hz, 1H), 7.03 (d, J 2.1 Hz, 1H), 6.97 (dd, J 8.4, 2.1 Hz, 1H), 4.53 (d, J= 4.6 Hz, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.07, 169.81, 154.14, 136.18, 135.86, 133.44, 131.11, 129.23, 125.00, 118.91, 115.96, 105.49, 43.32.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
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