Tag: M.W=200-300

Application of 104618-32-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 104618-32-8 name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 14 3-Amino-6-n-butyloxy-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (1.12 g) with 4-n-butyloxyphenyl hydrazine hydrochloride (1.00 g) and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.47 g), mp 227-229 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
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Application of 6941-75-9, 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 6941-75-9 as follows.

Step 1: tert-butyl 5-bromo-1,3-dihydro-2H-isoindole-2-carboxylate To a solution of 5-bromo-1H-isoindole-1,3(2H)-dione (4 mmol) in THF (10 mL) was added borane-dimethyl sulfide complex (2M in THF, 14 mL) at 0 C. The reaction mixture was allowed to stir at reflux overnight and was then cooled to 0 C. The reaction mixture was quenched by the slow addition of MeOH (10 mL) and then 2N HCl (10 mL). The reaction mixture was allowed to stir at reflux for 3 hr and then concentrated. Water (10 mL) was added to the residue. Remaining starting material was removed by extraction with DCM. To the aqueous solution was added 4N NaOH until pH>9. The solution was extracted with DCM. The organic solutions from this basic extraction were combined, dried over Na2SO4, filtered and concentrated to give 5-bromoisoindoline, which was dissolved in THF (20 mL). To this solution was added potassium carbonate (8 mmol) in water (1 mL), and BOC2O. The reaction mixture was allowed to stir at rt over the weekend. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 5-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (2.5 mmol, 60%).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
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These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. Safety of 2,3-Dioxoindoline-5-sulfonyl chloride

Step 3: 5-({(2S)-2-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}sulfonyl)-1H-indole-2,3-dione The title compound was prepared from 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride and 1-methyl-4-[(2S)-pyrrolidin-2-ylmethyl]piperazine according to a procedure similar to that of step 1 of Example 12. NMR (400 Mz, DMSO-d6): consistent.

The synthetic route of 2,3-Dioxoindoline-5-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
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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 923590-95-8 as follows. Application In Synthesis of 4-Bromoisoindoline hydrochloride

3. Kumada Coupling of Bromo-Iso-Indole [0258] bromoisoindoline HCl salt (25 g, 106.6 mmol), Pd(OAc)2 (0.199 g, 0.533 mmol), and the ligand (di-tert-butylneopentylphosphonium tetrafluoroborate, 0.325 g, 1.066 mmol). PhMe (toluene) (450 mL, de-oxygenated via sparging with N2) was then added, and the resulting slurry was then cooled to Ti=5 C. using an external bath. Allylmagnesium chloride (1.7 N in THF, 207 mL, 351.8 mmol) was charged to an addition funnel via cannula, and then added at a rate such that Ti<20 C. The resulting solution was then was heated to Ti=45-50 C. [0260] After 16 hours, LC showed >99% conversion of starting material. The reaction was cooled to room temperature, and then was inverse-quenched into 250 mL of 15% aqueous citric acid. The phases were separated, and the aqueous phase containing the product was held while the dark organic phase was rejected. The extractor that contained the aqueous phase was charged with 125 mL of PhMe. The pH of the aqueous phase was adjusted by the addition of 115 mL of NH4OH. The phases were separated, and the organic phase containing the product was held while the aqueous phase was rejected. The organic phase was washed with 20 mL of 15% aqueous NaCl. The PhMe solution was concentrated with azeotrope to a 10 volume solution (KF<2000 ppm H2O). [0261] This PhMe solution of product was transferred to 250 mL flask with overhead stirring. An addition funnel was charged with 17.5 mL of 5.33 M HCl in IPA (5.3 M), which was added slowly over 20 minutes. The resulting slurry was aged for 30 minutes at Ti=40 C., and then was gradually cooled to Ti=20-22 C. over 30 minutes. After aging for 1 hour, the slurry was slowly cooled to Ti=0 C. over 30 minutes by use of an external bath. After 30 minutes, the slurry was filtered. The cake was washed with 16 mL of cold (Ti=-10 vC) 14:2 PhMe:IPA. The cake was then washed with 15 mL of ambient temperature (Ti=22 C.) MTBE. After drying, 7.6 g of allyl isoindoline was isolated as an off white solid. The isolated product assayed for 98.7 wt %. According to the analysis of related databases, 923590-95-8, the application of this compound in the production field has become more and more popular. Reference:
Patent; Chen, Cheng; Kong, Jongrock; Humphrey, Guy; Dolman, Sarah; Li, Hongmei; Tudge, Matthew T.; Yong, Kelvin; Xiang, Bangping; Zacuto, Michael; US2013/274463; (2013); A1;,
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Related Products of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A mixture of isatin 2 (0.8 mmol), malononitrile (1.0 mmol) and Ca(OH)2 (0.8 mmol, 59.2 mg) in 5.0 mL of methanol was stirred at roomtemperature for 10 min followed by the addition of chrysin 1(0.5 mmol), which was stirred under reflux for 8 h. After completion ofthe reaction, as indicated by TLC, the mixture was cooled to roomtemperature and then purified by flash chromatography to afford thecorresponding product 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Zhang, Wen-Hui; Chen, Shuang; Liu, Xiong-Li; Feng, Ting-Ting; Yang, Wu-De; Zhou, Ying; Bioorganic and Medicinal Chemistry; vol. 27; 22; (2019);,
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Related Products of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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.

To a solution of 5-fluoropyridine-3-boroniotac acid (CASNo. 872041-86-6, 80mg, 0 57mmol) in 1 ,2-dimethoxyethane (0 7 mL) was added water (0.3 mL) and ethanol (0,2 mL). The solution was then charged with sodium carbonate (60 mg, 0.57mmol), 5-bromo-1-methyl- 1 ,3-dihydro-mdol-2-one (CASNo. 20870-90-0, 132 mg, 0.57 mrnol), and diotachlorobis(triphenylphosphiotane)palladium (II) (CASNo. 13965-03-2, 20.3 mg, 0 029 mmol) The reaction vessel was sealed and is heated by microwave irradiation at 150 C for 10 minutes. The reaction mixture was cooled to room temperature, filtered and concentrated. The resulting residue was partially punfied by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water w/ 0.1% TFA) Final purification was accomplished via silica gel flash chromatography (methanol-dichloromethane. 0 to 7%) to afford 5-(5-fluoro-pyriotadin-3-yl)-1-methyl-1 3-dihydro-iotandol-2-one; MS. (ES+) m/z 243 (M+Hr; 1H NMR (400 MHz, DMSO-Cf6) delta ppm 3 18 (s, 3 H) 3,64 (s, 2 H), 7 13 (d, J-7.% Hz1 1 H), 7,73 – 7 77 (m, 2 H)1 8.03 (d, J=9 7 Hz, 1 H), 8 53 (d, J=2 7 Hz, 1 H), 8.79 (s, 1 H),

The synthetic route of 20870-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Some common heterocyclic compound, 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, molecular formula is C10H8ClNO2, 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. name: 5-(2-Chloroacetyl)indolin-2-one

A suspension of 93 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80 to 90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL ethanol. The solid was dissolved in 90 mL 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid. After standing overnight the filtrate yielded 2 g of 5-carboxy-2-oxindole as a yellow solid. The crude dark brown product was dissolved in hot methanol, the insoluble material removed by filtration and the filtrate concentrated to give 5.6 g of 5-carboxy-2-oxindole as a brown solid. The combined yield was 97%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65435-04-3, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8BrNO

General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.

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; Zhang, Ji-Quan; Li, Shu-Min; Wu, Chun-Feng; Wang, Xing-Lan; Wu, Ting-Ting; Du, Yao; Yang, Yuan-Yong; Fan, Ling-Ling; Dong, Yong-Xi; Wang, Jian-Ta; Tang, Lei; Catalysis Communications; vol. 138; (2020);,
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Reference of 959235-95-1,Some common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (2.5 g, 12.3 mmol), 2- (4-chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (2.47 g, 12.3 mmol), HATU (7 g, 18.5 mmol) and diisopropylethylamine (6.1 mL, 36.9 mmol) in DMF (40 mL) was stirred at room temperature for 4 h. Water and EtOAc were added. The organic layer was separated, washed with water, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc 85/15). The pure fractions were combined and the solvent was concentrated under reduced pressure to give, after crystallization from CHsCN/heptane, 2-(4-chloro-2- methoxyphenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 17c (4.3 g).

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

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); 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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H3BrFNO2

H202 (10.0 mL, 98 mmol) was added to a solution of 6-bromo-7-fluoroindoline-2,3-dione (5.4 g, 22.13 mmol) and sodium hydroxide (27.7 mL, 55.3 mmol) in water (20 mL) at 0 C and the reaction mixture was stirred at 0 C for 2 hr. The reaction mixture was acidified by 2N HCI until the pH = 6. The solid was collected by filtration and dried in vacuo to give 2-amino-4-bromo-3-fluorobenzoic acid (4.8 g, 20.51 mmol, 93 % yield) as a yellow solid. LCMS: [M+H] 234.1 .

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 1336963-95-1.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JIN, Qi; POHLHAUS, Denise Teotico; SPLETSTOSER, Jared; (320 pag.)WO2017/98440; (2017); A1;,
Indoline – Wikipedia,
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