Tag: M.W=100-200

These common heterocyclic compound, 6341-92-0, name is 6-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

Example 109 2-(6-Chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid thiazol-2-ylamide A mixture of sodium hydride (60% in oil, 264 mg) in N,N-dimethylformamide at 0 C. was treated with a solution of 6-chloro-1H-indole-2,3-dione (1.0 g) in N,N-dimethyl formamide (total volume is 25 mL). The reaction mixture was then stirred for 30 min at 0 C. After this time, the reaction mixture was treated with 2-bromo-4-methyl-pentanoic acid methyl ester (prepared as in Example 9, 1.38 g) and stirred for another 1 h at 0 C. The reaction mixture was then allowed to warm to room temperature and stirred for 3 h. After this time, the reaction was diluted with water and extracted with methylene chloride. The organic layers were combined and then dried over sodium sulfate, filtered to remove the drying agent and the filterate concentrated in vacuo. The residue obtained was then purified by silica gel column chromatography to afford 2-(6-chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid methyl ester (1.3 g, 76%).

The synthetic route of 6-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
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Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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. Application In Synthesis of 5-Nitroindolin-2-one

A. A suspension of 5-nitroindolin-2-one (2.0 g, 11.13 mmol), and 10% palladium on carbon (500 mg) in methanol (100 mL) was hydrogenated for 2 hours under 45 psi. The reaction mixture was filtered through celite and the resulting cake was washed with methanol. The filtrate was concentrated to afford 5-aminoindolin-2-one as a tan-colored solid (1.6 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Patent; Schering Aktiengesellschaft; US2005/90541; (2005); 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. 65826-95-1, name is 5-Methylindoline, A new synthetic method of this compound is introduced below., Product Details of 65826-95-1

EXAMPLE 54 2-(5-Methylindolin-1-yl)benzonitrile A slurry of 5-methylindoline (31 g, 0.23 mole), sodium hydride (11.3 g, 60% in oil) and dimethylsulfoxide (120 ml) was stirred at room temperature for 1 hour. A solution of o-fluorobenzonitrile (31 gm, 0.25 mole) in dimethylsulfoxide (25 ml) was added dropwise at a temperature below 20 C. Upon completion of the addition, the mixture was stirred for 2 hours at room temperture. The reaction mixture was partitioned between methylene chloride (700 ml) and ice-water (700 ml). The dichloromethane solutions were separated. The aqueous phase was extracted with dichloromethane (2 times, 600 ml). The combined dichloromethane solutions were washed with 2N hydrochloric acid (2 times, 500 ml), water (500 ml), brine (2 times, 400 ml), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dissolved in ethanol (300 ml) and heptane (100 ml), and chilled in a freezer. The precipitate was collected. The mother liquor was concentrated and purified by flash chromatography on a silica gel column (400 g, 230-400 mesh) eluted with hexane:dichloromethane (3:1, 3 l); hexane:dichloromethane (1:1, 2 l) and dichloromethane (2 l). The fractions containing product were pooled and concentrated to yield 33 g (73% overall yield). The analytical sample was prepared by high-pressure liquid chromatography (Water Associates Prep 500, 10 g, 2 chamber, elution with hexane:dichloromethane, 9:1, 12 l) followed by crystallization from ethanol, mp 59-60 C. ANALYSIS: Calculated for C16 H14 N2: 82.02%C 6.02%H 11.96%N. Found: 82.47%C 6.08%H 12.10%N.

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; Hoechst-Roussel Pharmaceuticals Inc.; US4663453; (1987); A;,
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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 7699-18-5 as follows. COA of Formula: C9H9NO2

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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Related Products of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

The intermediate from Step D was esterified by heating in acidic methanol overnight. The resulting solution was concentrated under vacuum and the residue was dissolved in hot ethanol (75 mL). Methanol (20 mL) was added to redissolve some material that precipitated as the solution cooled. Sodium nitrite (1.50 g) was added, followed by concentrated hydrochloric acid (5 mL). The reaction was stirred for 2 h, and a further concentrated hydrochloric acid (2 mL) was added. The reaction was stirred overnight. Volatiles were removed under reduced pressure, water added, and the resulting yellow orange product was isolated by filtration and dried under vacuum to give the intermediate (2.1 g) as a yellow orange solid. [MH]+=221.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
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Electric Literature of 89-40-7, The chemical industry reduces the impact on the environment during synthesis 89-40-7, name is 5-Nitroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The substrate (0.5 mmol), NiPd/MIL-101 catalyst (0.023g, Pd 0.2 mol%), and ethyl acetate (4 mL) were added to a Schlenk tube, and the mixture was vigorously stirred with an affixed hydrogenation balloon at room temperature. Following the reaction, the solid catalyst was removed from the solution by filtration and washed with ethyl acetate. The product yields were determined by gas chromatography-mass spectrometry (GC/MS, Shimadzu GCMS- QP5050A) with a 0.25 mm ¡Á 30 mDB-WAX capillary column. Parameters were as follows: initialoven temperature, 100 C, 1 min; ramp, 20 C/min; final temperature, 280 C; final time, 5 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, 5-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jian, Siping; Li, Yingwei; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 37; 1; (2016); p. 91 – 97;,
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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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 32692-19-6

5-Nitro-1-(2-(pyrrolidin-1-yl)ethyl)indoline (3) A solution of compound 2 (500 mg, 3.05 mmol) in DMF (10 mL) was treated with NaH (390 mg, 9.75 mmol, 60% wt in mineral oil) at 0 C. resulting in a bright orange suspension. The mixture stirred for 10 minutes, then 2-chloroethyl-pyrrolidine hydrochloride (566 mg, 3.33 mmol) was added and the reaction turned into a bright red suspension. The reaction was heated to 90 C. for 1 hour. After 1 hour, the reaction was allowed to cool to room temperature. Then it was diluted with water (20 mL), transferred to a separatory funnel and extracted with ethyl acetate (2*15 mL). The combined the organic layers were washed with brine (3*5 mL), dried (Na2SO4), filtered and concentrated. The residue was subjected to flash chromatography on silica gel using: 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 to give a brown solid (400 mg, 50%). 1H-NMR (DMSO-d6) delta 7.96 (dd, J=2.4, 9.0 Hz, 1H), 7.80 (d, J=2.1 Hz, 1H), 6.47 (d, J=9.0 Hz, 1H), 3.73 (t, J=9.0 Hz, 2H), 3.41 (t, J=6.9 Hz, 2H), 3.04 (t, J=8.1 Hz, 2H), 2.62 (t, J=6.9 Hz, 2H), 2.58-2.48 (m, 4H), 1.70-1.64 (m, 4H).

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
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Related Products of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

3-lodobenzoic acid (248 mg, 1.0 mmol), isoindoline (284 uL, 1.5 mmol), and triethylamine (420 uL, 3.0 mmol) were dissolved in 10 ml. of CH2CI2 and treated with HOBt (203 mg, 1.5 mmol) and EDC (288 mg, 1.5 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1N HCI, and brine. The organic layer was dried (MgSO4), filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (CH2CI2/Et0Ac) to yield 304 mg (87%) of the product as a tan solid. MS (+ESI): m/z 349.9 [M+H]+.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
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317-20-4, name is 7-Fluoroisatin, 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. HPLC of Formula: C8H4FNO2

Weigh rapamycin (0.05mmol), isatin 3j (0.10mmol) and rhodium octanoate dimer(0.0005mmo),They were placed in a reaction flask, 2.0 mL of dry dichloromethane was added, and after stirring at room temperature for 5 minutes,Phenyldiazo 2a (0.10 mmol) was weighed and dissolved in dry dichloromethane (1.0 mL), and slowly added dropwise to the reaction system (about 1 hour), and stirring was continued for half an hour.The solvent was removed by rotary evaporation to give a crude product. The rapamycin analog I-j was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 85%.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ha Yao Cihang Pharmaceutical Co., Ltd.; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Duan Yanwen; Huang Yong; Qiu Lin; Wen Zhongqing; Su Meng; (38 pag.)CN109776571; (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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 7699-18-5

General procedure: 4.4.10 (Z)-5-methoxy-3-((2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-6-yl)methylene) indolin-2-one (5j) Compound 5j was prepared according to the method described for compound 5a, employing aldehyde 11c (145 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81, 0.5 mmol) to obtain the pure product 5j as a yellow solid (132 mg, 61%); mp: 293-295 C; IR (KBr): 3420, 3160, 2355, 1672, 1618, 1470, 1328, 1113, 1015, 915, 845, 741 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.48 (bs, 1H), 9.22 (s, 1H), 8.44 (d, J = 8.1 Hz, 2H), 8.17 (s, 1H), 7.99 (s, 1H), 7.96 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.3 Hz, 1H), 7.45 (s, 1H), 6.87-6.68 (m, 2H), 3.79 (s, 3H); 13C NMR (75 MHz, CDCl3 + DMSO-d6): delta 168.8, 154.6, 153.8, 138.4, 137.3, 136.4, 134.0, 133.4, 127.2, 126.6, 125.9, (q, J = 2.7 Hz), 125.2, 125.0, 122.9, 121.9, 114.9, 110.2, 109.6, 108.6, 105.5, 55.2; MS (ESI): m/z 436 [M + H]+; HRMS (ESI): calcd for C24H17ON3F3 m/z 436.12073 [M + H]+; found 436.12437.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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