Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 99365-40-9, Product Details of 99365-40-9

Reaction condition three: Under the protection of nitrogen,6-bromopyridin-2-one (212.0 mg, 1.0 mmol),Potassium carbonate (276 mg, 2 mmol),Tetrabutylammonium bromide (33 mg, 0.1 mmol) was placed in a two-neck reaction flask.Sealing the reaction unit,The nitrogen gas was exchanged three times and a nitrogen balloon was inserted.Inject 22 mL of tetrahydrofuran,Stir at 85 C for 30 min,Then slowly inject 3 mL of bromohexane,Stir at 85 C for 8 h.After the reaction was slowly cooled to room temperature, it was poured into ice water and quenched. The organic phase was extracted with dichloromethane and washed three times with water.After suction filtration, the organic phase was concentrated under reduced pressure in vacuo to give a crude material, which was purified by column chromatography chromatography (DCM/PE = 1:1).To give a white waxy solid compound 1-hexyl-6-bromo – indol-one (172mg),The yield was 58.1%.

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, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Lai Wenyong; Meng Cheng; Li Xiangchun; Huang Wei; (15 pag.)CN108948026; (2018); A;,
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Application 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.

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-(Trifluoromethoxy)indoline-2,3-dione

0.4 mmol of 5-trifluoromethoxyisatin, 0.2 mmol of antipyrine, 0.04 mmol of imidazole and 1 mL of water were mixed, and the reaction was stirred under an oil bath of 80 C for 29 hours.Then, the obtained reaction system was cooled to room temperature, extracted with dichloromethane, and the organic phase was collected. The obtained organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (mobile phase: petroleum ether / ethyl acetate volume ratio) In the order of 4/1, 3/1, 2/1 and 1/1), the title compound I-7 (yellow solid, yield 65%, purity 99.8%) was obtained.

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 169037-23-4.

Reference:
Patent; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 6941-75-9

A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g ,0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-l,3-dione (5 g, 22mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HC1. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2S04 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261C; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J = 9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]”); IR (thin film) 1684, 3246, 606 cm-1.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William, C.; HUNTER, James, E.; WATSON, Gerald, B.; PATNY, Akshay; IYER, Pravin, S.; BORUWA, Joshodeep; WO2014/100206; (2014); A1;,
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Related Products of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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 cis-N-benzyl-2,5-bis(methoxymethyl)pyrrolidine (18a) (620 mg, 2.49 mmol, 1.00 equiv.) and 10% Pd/C (62 mg, 10% w/w) in MeOH (12 mL) was stirred in an autoclave at ambient temperature under H2 atmosphere (20 atm) for 6 h. After this time, the mixture was filtered through Celite and washed again with MeOH. The solvent was removed under reduced pressure to obtain the corresponding unprotected bis(methoxymethyl)pyrrolidine as a light yellow oil. The solution of obtained free amine cis-2,5-bis(methoxymethyl)pyrrolidine and DIPEA (766 muL, 4.40 mmol, 2.00 equiv.) in CHCl3 (5 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.08 g, 4.40 mmol, 2.00 equiv.) in CHCl3/THF (1:1, 50 mL) at room temperature. The resulting mixture was stirred further for 2 h and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 90% EtOAc in cyclohexane) to yield a yellow solid (723 mg, 1.96 mmol, 89%). M.p. 168 C. 1H NMR (400 MHz, DMSO-d6): delta = 11.46 (br s, 1H, 1-NH), 8.05 (dd, 3JH,H = 8.3 Hz, 4JH,H = 2.0 Hz, 1H, 6-CH), 7.80 (d, 4JH,H = 1.9 Hz, 1H, 4-CH), 7.09 (d, 3JH,H = 8.3 Hz, 1H, 7-CH), 3.73-3.58 (m, 2H, 12-CH, 15-CH), 3.52-3.20 (m, 4H, 16-CH2, 19-CH2), 3.37 (s, 6H, 18-CH3, 21-CH3), 1.78-1.62 (m, 2H, 13-CHa, 14-CHa), 1.57-1.37 (m, 2H, 13-CHb, 14-CHb) ppm. 13C NMR (100 MHz, DMSO-d6): delta = 182.9 (3-CO), 159.4 (2-CO), 153.6 (8-CN), 136.7 (6-CH), 130.8 (5-CSO2), 123.1 (4-CH), 118.1 (9-CCO), 112.7 (7-CH), 74.4 (2C, 16-CH2, 19-CH2), 59.9 (2C, 12-CH, 15-CH), 58.4 (2C, 18-CH3, 21-CH3), 26.9 (2C, 13-CH2, 14-CH2) ppm. HRMS (ESI+, MeOH): m/z = 391.0931 [M + Na]+, 423.1194 [M + Na + MeOH]+; calcd. 391.0934 for C16H20N2O6S + Na, 423.1196 for C16H20N2O6S + Na + MeOH.

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

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
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Reference of 193354-13-1, 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. 193354-13-1 name is 5-Iodoindolin-2-one, 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.

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 ML of methanol, 15 ML of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide.. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated.. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane).. The fractions containing product were concentrated and allowed to stand.. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Iodoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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Application of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

[0715] Step 12: Synthesis of S-(5-(1,3-dioxoisoindolin-2-yl)pentyl)ethanethioate (15-k) To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). 1H NMR (400 MHz, CDCl3): delta 7.84 (dd, J = 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J = 5.5 Hz, 3.1Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 2.85 (t, J = 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M++1).

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

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; LADNER, Robert D.; (345 pag.)WO2018/128720; (2018); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0C. NaH (38 mg, 0.94 mmol, 60 wt.% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified silica chromatography, eluting with 0-20% EtOAc in hexanes. Desired fractions were concentrated in vacuo to afford the title compound, 1-23. LRMS (ESI) calc’d for Ci0H8BrF3NO [M+H]+: 294, found: 294.

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; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
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Electric Literature of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Reference of 1336963-95-1, A common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, molecular formula is C8H3BrFNO2, 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.

EXAMPLE 73-(1 ,4′-bipiperidin-1 ‘-ylmethyl)-7-bromo-8-fluoro-//-(1 -phenylcvclopropyl)-2-r3- (trifluorometh l)phenyll-4-quinolinecarboxamide7-bromo-8-fluoro-3-methyl-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxylic acidTo a solution of 6-bromo-7-fluoro-1 H-indole-2,3-dione (19 g, 77.8 mmol) in THF (200 mL) was added a solution of KOH (21.8 g, 389 mmol) in water (100 mL) dropwise. After the addition was complete, 1-[3-(trifluoromethyl)phenyl]-1 -propanone (15.73 g, 77.8 mmol) was added and the mixture was heated to reflux for 1.5 h. The THF was removed in vacuo, and the remaining aqueous solution was washed with diethyl ether (3 x 100 mL) and acidified with 1 N HCI to pH 2. The precipitate was collected by filtration to afford 7-bromo-8-fluoro-3- methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (16 g, 68% yield).

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
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