Tag: M.W=200-300

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-(Trifluoromethoxy)indoline-2,3-dione

Weigh 5-trifluoromethoxyBlush1.0g (0.0043mol),5-chloroindole anhydride 0.9g (0.0045mol) was added to a 100ml three-necked flask containing magnetons.Then add 40 ml of chloroform to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h,After the reaction is over, stop heating and wait for cooling.The crude product was obtained as a yellow solid powder by suction filtration.The product was washed 3 times with 10 ml of ethanol.Obtaining a pure product yellow solid powder,drying,Weighing 1.12g,The yield was 70.9%.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Combine 6-bromo-2, 3-dihydro-isoindol-1-one (0.200 g, 0.94 mmol), bis- pinocalatodiboron (0.264 g, 1.04 mmol), palladium (II) acetate (16 mg, 0.07 mmol) and tricyclohexylphosphine (26 mg, 0.09 mmol) in a 50 mL flask. Add acetonitrile (10 mL) and cesium fluoride (0.428 g, 2.82 mmol); fit flask with condenser and heat in a 90 C oil bath for 1 hour. Cool to room temperature and add trifluoro-methanesulfonic acid 6- methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (0.200 mg, 0.38 mmol), palladium (II) acetate (13 mg, 0.05 mmol) and tricyclohexylphosphine (20 mg, 0.07 mmol), cesium fluoride (0.172 g, 1.13 mmol) and acetonitrile (5 mL). Heat mixture in a 90 C oil bath for 1 hour. Cool reaction to room temperature and filter through celite and wash celite pad with ethyl acetate (60 mL). Concentrate the filtrate and pre-adsorb the crude product onto silica gel. Chromatograph the residue on a Si02 column eluting the material with methanol in dichloromethane (0 to 15%) to give 110 mg of the title compound (57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
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Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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-Bromoisoindolin-l-one (CAS 675109-26-9) (1.61 g, 7.58 mmol, 1.05 equiv.) was suspended in 32 ml of THF and cooled to 0-5C. Sodium hydride (60% dispersion in mineral oil) (318 mg, 7.94 mmol, 1.1 equiv.) was added at 0-5C. The reaction mixture was stirred at room temperature for 15 minutes and then cooled to 0-5C. Methyl (2RS)-2-bromo-2-(5-fluoro-2- methoxyphenyl)acetate (CAS 1368458-30-3) (2.00 g, 7.22 mmol) dissolved in 8.0 ml of THF was added dropwise at 0-5C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4CI- solution and extracted with ethyl acetate. The aqueous layer was backextracted with ethyl acetate. The organic layers were washed with water and brine. The organic layers were combined, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:heptane 0: 100 to 50:0 gradient to obtain the desired methyl (2RS)-2-(6-bromo-l-oxo- isoindolin-2-yl)-2-(5-fluoro-2-methoxy-phenyl)acetate (2.202 g, 75 % yield) as a yellow foam, MS: m/e = 408.0/410.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; C4 THERAPEUTICS, INC.; JAESCHKE, Georg; RICCI, Antonio; RUEHER, Daniel; STEINER, Sandra; DUPLESSIS, Martin; NAGEL, Yvonne Alice; KUHN, Bernd; (60 pag.)WO2018/220149; (2018); A1;,
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Related Products of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

N-(5-bromopentyl)phthalimide (1.2g, 4mmol) and thiomorpholine 1,1-dioxide (1.08g, 80mmol) and DIPEA (2ml, 11mmol) was added 10mL i-PrOH, the temperature was raised to 105 deg. C stirred for 16 hours. LCMS traced the reaction. After completion of the reaction it was concentrated, 50ml of water was added, sonicated, and filtered to give a white solid N-(5-(1,1-dioxothiomorpholin-4-yl)pentyl)phthalimide (1.0g, 97% yield).

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; Shenzen Chipscreen Biosciences Ltd.; Lu, Xianping; Liu, Jindi; Yang, Qianjiao; Li, Zhiping; Pan, Desi; Shan, Song; Zhu, Jiangfei; Wang, Xianghui; Liu, Xiangheng; Ning, Zhiqiang; (30 pag.)CN105481778; (2016); A;,
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Synthetic Route of 20870-90-0, 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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under N2, sodium ( 0.5 g ) was reacted with 30 ml ethanol. When the solution was clear,2.9 g N-Me oxindole was added followed by 3.1 g diethyl carbonate and the resulting reactionmixture was refluxed for 15 hours. Then cooled to room temperature and added to 3Nhydrochloric acid solution ( pH = 2 ). The resulting solution was extracted with ether for threeEntry Catalyst time (h) yieldb(%) drc eed(%)1 3e 5 96 72:28 38e/382 3f 8 96 74:26 21e/33 3g 2 99 73:27 11e/334 3h 8 96 71:29 6e/335 3i 2 95 59:41 1e/26 3j 10 94 68:31 44/1e7 3k 2 93 67:33 1/18 3l 72 61 69:31 8/1times. The organic extracts were combined and dried over magnesium sulfate. Thenconcentrated in vacuo and washed with petroleum ether to give 2.7 g2-oxindole-3-carboxylates 1a (61%) as light yellow solid.

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-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Jing; Jia, Li-Na; Peng, Lin; Wang, Qi-Lin; Tian, Fang; Xu, Xiao-Ying; Wang, Li-Xin; Tetrahedron; vol. 70; 21; (2014); p. 3478 – 3484;,
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Related Products of 3335-98-6, 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. 3335-98-6 name is 1-Phenyloxindole, 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.

Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5 C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3¡Á200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyloxindole, and friends who are interested can also refer to it.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54631; (2005); A1;,
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Reference of 954-81-4, A common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

According to the Scott?s method4, ethyl acetoacetate (1.30 g, 10.0 mmol) was added to a solution of sodium ethoxide in EtOH, prepared from dist. EtOH (8 mL) and sodium (230 mg, 10.0 mmol). To the mixture was added N-(5-bromopentyl)phthalimide (4) (2.96 g, 10.0 mmol), and refluxed under argon for 6 hours. After cooling, the reaction mixture was neutralized with 2N HCl, and the ethanol was removed under reduced pressure. The residue was dissolved in H2O (50 mL), and extracted with Et2O (3 x 40 mL). The organic phase was combined, dried over Na2SO4, and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane : AcOEt = 2 : 1) to give 54 (2.33 g, 79%) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 1.27 (t, 3H, J = 7.3 Hz), 1.32-1.37 (m, 4H), 1.66-1.71 (m, 2H), 1.82-1.87 (m, 2H), 2.23 (s, 3H), 3.40 (t, 1H, J = 7.3 Hz), 3.67 (t, 2H, J = 7.3 Hz), 4.20 (q, 2H, J = 7.3 Hz), 7.72 (dd, 2H, J = 5.5 Hz, 3.3 Hz), 7.84 (dd, 2H, J = 5.5 Hz, 3.3 Hz). 13C NMR (75 MHz, CDCl3) delta 13.9, 26.4, 26.8, 27.8, 28.1, 28.6, 37.6, 59.6, 61.1, 123.0, 131.9, 133.7, 168.2, 169.6, 202.9. MS (FAB) 346 (M+H)+. TLC: Rf 0.40 (Hexane : AcOEt = 2 : 1).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamo, Masahiro; Tateishi, Hiroshi; Koga, Ryoko; Okamoto, Yoshinari; Otsuka, Masami; Fujita, Mikako; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 43 – 45;,
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Related Products of 6941-75-9, A common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

A mixture of 4-bromophthalic anhydride (25 g) in formamide (75 ml) was heated at 2000C for 16 hours then allowed to cool to room temperature. The reaction mixture was diluted with water (200 ml), filtered, the filter cake was washed with water then diethyl ether and sucked dry to give 20.85 g of light mustard solid.280 ml of 1 M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at O0C then heated at reflux overnight. The reaction was cooled to O0C then treated cautiously with methanol (100 ml) followed by 2M HCI (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (x3). The aqueous was basified with 2M NaOH then extracted with DCM (x3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1 H1 d), 7.20 (1H, d), 4.05 (4H, s).

The synthetic route of 6941-75-9 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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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. 400727-63-1, name is tert-Butyl 5-nitroisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 400727-63-1

To 560mg of P13 in 20 mL of ethanol was added 56 mg of 10% Pd/C and the mixture shaken under 35 psi of hydrogen gas for 15 minutes. The mixture was filtered and evaporated to dryness yielding 516 mg of P14.

The synthetic route of 400727-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; CHELLIAH, Mariappan, V.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; EAGEN, Keith, A.; GUO, Zhuyan; CLASBY, Martin, C.; XIA, Yan; JAYNE, Charles, L.; DWYER, Michael; KEERTIKAR, Kartik, M.; CHAN, Tin-Yau; WANG, Li; WO2011/17296; (2011); A1;,
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Related Products of 1677-48-1, The chemical industry reduces the impact on the environment during synthesis 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

A 250 mL round bottom flask was charged with 5,6-dichloroisatin(5,6-dichloroisatin) (500 mg, 2.32 mmol)was dissolved in methanol (MeOH) (92.80 ml), and then, Indoxyl acetate (405.48 mg, 2.315 mmol) Sodium carbonate (Na2CO3) (637.83 mg, 6.02 mmol) was added thereto, followed by stirring at 65 DEG C for 12 hours. The reaction is terminated using TLC (Rf = 0.4, ethyl acetate / hexane = 1/2 (v / v)) and the product is allowed to cool down on ice until a lump of crystals is formed. After the crystals are formed, the solvent is removed by filtration, the filtrate is discarded, and the product is washed several times with a solvent (ethanol / water = 1/1 (v / v)). The product was filtered and dried in a vacuum pump and used in the next step without further purification.

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, 5,6-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CK BIOTECH; C Kei Bio Tech Co., Ltd.; CHOI KANG YELL; Choi Gang-yeol; HAN GYOON HEE; Han Gyun-hui; LEE CHUL HO; Lee Cheol-ho; SEO SEOL HWA; Seo Seol-hwa; (31 pag.)KR2018/119941; (2018); A;,
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