Tag: M.W=300-400

Application of 1201923-48-9, 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. 1201923-48-9, name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture [(S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(3-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester (1.203 g, 3 mmol) and trifluoroacetic acid-dichloromethane (15 mL, 2:1) was stirred at room temperature for 1 hour and then concentrated under reduced pressure to give crude 2-[(S)-2-amino-3-(3-fluoro-phenyl)-propyl]-isoindole-1,3-dione trifluoroacetic acid salt. (Yield 1.516, 123%).

The synthetic route of (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); 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. 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, A new synthetic method of this compound is introduced below., SDS of cas: 88150-75-8

Example 8a synthetic process of amlodipine besylate,The difference from Embodiment 1 is thatStep three is: in the reaction tank,Into a toluene solution of 4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate,Distilled under reduced pressure at 70 C,Fill the water separator and continue to reflux under reduced pressure.Until the water content in the reflux liquid is ?0.2%, the temperature is lowered to 35 C, 27 kg of 2-chlorobenzaldehyde is added, and the internal temperature is maintained at 35 C.Add 1.5 kg of hexahydropyridine and stir for 30 minutes.Under the condition of 65 C, -0.09 Mpa, the water was refluxed under reduced pressure for 12 hours or more, the temperature was lowered to 35 C, and 120 kg of water was added.Stir,Let stand for 30 minutes,Layered, the lower aqueous layer is recovered, and the upper layer is a toluene solution of 2-(2-chloroindol)-4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate; The yield of amlodipine was 91.2%, and the purity was 99.5%.

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; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Liu Lijuan; Gao Huanhuan; Yu Yaoying; (13 pag.)CN108456160; (2018); A;,
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These common heterocyclic compound, 17826-05-0, name is 5,6-Dibromoindoline-2,3-dione, 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. Application In Synthesis of 5,6-Dibromoindoline-2,3-dione

General procedure: Water (15 mL) was added to a mixture of 1.0 mmol of isatin derivative, 1.2 mmol of creatinine (for 2p, 2.3 mmol of creatinine) and 1 mol% of HAuCl4 and the resulting suspension was heated to reflux for 30 min. The clear reaction mixture was cooled to 15-20 C. The precipitated aldol product was filtered and washed with copious amount of water and then with methanol and ethyl acetate (EtOAc). The obtained product was thoroughly dried under vacuum to afford the pure product 2a-2p.

The synthetic route of 5,6-Dibromoindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Parthasarathy; Ponpandian; Praveen; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 38; 5; (2017); p. 775 – 783;,
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Application of 88150-75-8, The chemical industry reduces the impact on the environment during synthesis 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, I believe this compound will play a more active role in future production and life.

Orthochlorobenzaldehyde (67.5 g, 0.48 M) was reacted with ethyl 4[2-(phthalimido)ethoxy acetoacetate (100 g, 0.31 M) in the presence of pyridine acetic acid in benzene at 80/82 C. for 12 hrs and cooled to room temperature. To the reaction mass water was added. Organic layer was separated and benzene was distilled out and the residue was washed with hexane.

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, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Purohit, Arun Kumar; Desai, Brahmader Chilu; Shete, Balasaheb Dashrath; Bagwan, Salim Abbas; US2004/44218; (2004); 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 17702-83-9 as follows. Application In Synthesis of 2-(8-Bromooctyl)isoindoline-1,3-dione

step 1 8-(Benzoxazol-2-ylsulfanyl)-octylamine To a round bottom flask with 2-mercaptobenzoxazole (2.14 g, 14.2 mmol) andDMF (100 mL) at room temperature was added K2CO3 (2.61 g, 18.9 mmol) followed by N-(8-bromooctyl)phthalimide (4.00 g, 11.8 mmol). The resulting solution was heated to 60° C. for 0.5 h and then cooled back to room temperature. At this point, the reaction mixture was quenched with H2O (100 mL) and then diluted with EtOAc (600 mL). The organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20percent EtOAc/petroleum ether gradient) to afford the thioether intermediate. To this thioether intermediate (3.02 g, 7.39 mmol) in MeOH (40 mL) at room temperature was added hydrazine monohydrate (0.860 mL, 17.7 mmol) and the resulting mixture was heated to reflux. After 18 h at this temperature, the reaction was concentrated, taken up in EtOAc (300 mL), and filtered to remove insoluble materials. This phthalimide byproduct was washed with excess EtAOc, and the filtrate was washed with H2O (40 mL) and brine (40 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (1.87 g, 57percent) as an oil; 1H NMR (CDCl3) delta1.14-1.67 (m, 12H), 1.72-1.92 (m, 2H), 2.69 (t, J=9.6 Hz, 2H), 3.32 (t, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 7.38-7.47 (m, 1H), 7.54-7.66 (m, 1H); mass spectrum [(+) ESI], m/z 279(M+H)+.

According to the analysis of related databases, 17702-83-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Butera, John A.; Caufield, Craig E.; Graceffa, Russell F.; Greenfield, Alexander; Gundersen, Eric G.; Havran, Lisa Marie; Katz, Alan H.; Lennox, Joseph R.; Mayer, Scott C.; McDevitt, Robert E.; US6214877; (2001); B1;,
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1498-88-0, name is 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline], 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. Quality Control of 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline]

General procedure: Trifluoroacetic acid (13.9 mmol) was added to a solution of the corresponding hybrid compound 1a-c (13.9 mmol) in toluene (10 ml). For neutralization of acid the equimolar quantity of triethylamine was added. Spectrophotometric measurements for solutions were carried out on an Agilent Cary 60 Bio spectrophotometer in a KU-1 quartz cell with optical path length of 2 mm. The isomerization was investigated at room temperature for 0.2 mm solutions of 1a-c.

The synthetic route of 1498-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tuktarov, Airat R.; Khuzin, Artur A.; Dzhemilev, Usein M.; Mendeleev Communications; vol. 29; 2; (2019); p. 229 – 231;,
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These common heterocyclic compound, 24566-80-1, name is 2-(10-Bromodecyl)isoindoline-1,3-dione, 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-(10-Bromodecyl)isoindoline-1,3-dione

A mixture of secondary amine from intermediate 1 C (3,6 g, 1 5 ,8 mmol), N-i I 0- ba>mod.ecyl)phthaUmide (4.4 g, 12.0 mmol), (2.0 g, 12.4 mmol) and 2CO3 (8.2 g. 59,4 ramol) in aeetomtrile (90 mL) was stirred at reflux overnight. After filtration, volatile components were evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (5% methanol in dichloromethane) to give the desired phthaltmido- protected i termediate 5b (6.0 g, 86% yield) as a Sight, brown oil, (0272) [0170] Compound 5b (2,9 g, 4.9 mmol) was refluxed with hydrazine hydrate (700 rag, 13.9 mmol in ethanol ( 100 mi.,) for 5 h. The solvent was evaporated and 10% aqueous solution of aOH {20 ml.) was added. The mixture was extracted with CH2CI2. dried over NasSO-t. and evaporated to give the primary amine ;V-(9-( 10-a.minodecy})-9~ (0273) azabkyco[3,3..1 “]nonan-3 -yl)-N -(2-methoxy-5-meihyiphenyl) carbamate 6b (2,2 g, 95% yield) as a Sight yellow oil. NMR (CDC ) 3 7.96 (s, 1H)S 7.14 (s, Eta), 6.72-6,80 (m, 2H), 5.10-5. J 8 (m, 1 H 3.84 (s, 3fl), 3.04-3.07 (m, 2H), 2.65-2.70 (m, 2H), 2.53-2.58 (ra, 2H), 2.39-2.49 (m, 2H), 2.29 (s, 3H>, 2.08-2.20 (in, 1 B), 1 .83- i .94 (ra 2.W). 1.18-1.54 (ra, 23H).

The synthetic route of 2-(10-Bromodecyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WASHINGTON UNIVERSITY; HAWKINS, William; MACH, Robert; SPITZER, Dirk; VANGVERAVONG, Suwanna; (84 pag.)WO2015/153814; (2015); A1;,
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These common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, 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. name: (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione

To suspension of 2-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-1H-isoindole-1,3(2H)-dione (170 gm) and potassium carbonate (59.3 gm) in dichloromethane (1500 ml) was added 1,1?-carbonylbis(1H-imidazole) (153.4 gm) at room temperature. Reaction mass was then stirred for 5 hr at room temperature. After completion of reaction, inorganic base is removed by filtration. The obtained filtrate is concentrated under reduced pressure to yield solid. To this solid tetrahydrofuran (850 ml) was added followed by stirring and filtration. The obtained solid is dried under vacuum for 4 hr at 50 C to obtain 2-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione. [Yield = 160 gm (88.2 %); Purity (HPLC) =99.65 %]

The synthetic route of (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEGAFINE PHARMA (P) LTD; MATHAD Vijayavitthal Thippannachar; PATIL NILESH SUDHIR, Nilesh; NIPHADE NAVNATH CHINTAMAN, Navnath; MALI ANIL CHATURLAL, Anil; BODAKE MAHENDRA BHAGIRATH, Mahendra; IPPAR SHARAD SUBHASH, Sharad; TALLA RAJESH, Rajesh; WO2013/121436; (2013); A2;,
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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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 17702-83-9

General procedure: To a solution of compound 5 (0.21 g, 10 mmol) in ethanol (20.0 ml), N-(3-bromopropyl)phthalimide (0.27 g, 10 mmol) was added, and the mixture was refluxed for 12 h. The reaction mixture was filtered to remove precipitated solid and the filtrate was concentrated under vacuum. The viscous residue was dissolved with 20 ml of ether, then washed with water and the ether layer was dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, the crude compound was chromatographed on silica gel to give O,O-diethyl-S-3-phthalimidopropyl phosphorothioate (0.12 g, 33.6percent yield) as light yellow oil.

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 17702-83-9.

Reference:
Article; Zhao, Qianfei; Xie, Ruliang; Zhang, Tao; Fang, Jing; Mei, Xiangdong; Ning, Jun; Tang, Yun; Bioorganic and Medicinal Chemistry Letters; vol. 21; 21; (2011); p. 6404 – 6408;,
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Application of 35197-64-9, 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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In this work, previously reported N-benzyl-2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanamide derivatives (25a-e) [44] were obtained by activating the carboxylic acid group of 24 (1 eqv) by using n-propanephosphonic acid anhydride (T3P, 50% in EtOAc, 1 eqv). The reaction was carried out under argon atmosphere for 2hat 0C in dry methylene chloride. Then, distilled triethylamine (1.2 eqv) and the appropriate N-benzylamine (1.1 eqv) were added to the reaction mixture [57]. The reaction was continued at room temperature for 12h. The products were purified by column chromatography over silica gel (DCM/acetone=9:1) to yield 25a-e as a white solid.

The synthetic route of 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?mudzki, Pawe?; Fija?kowski, ?ukasz; Furga?a, Anna; Gryz?o, Beata; Hoefner, Georg C.; Kulig, Katarzyna; Malawska, Barbara; Malawska, Katarzyna; Nowaczyk, Alicja; Podkowa, Adrian; Rapacz, Anna; Sa?at, Kinga; Wanner, Klaus T.; Zar?ba, Paula; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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