Tag: M.W=200-300

Electric Literature of 675109-26-9, 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. 675109-26-9 name is 6-Bromoisoindolin-1-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.

To a mixture of 6-bromoisoindolin-1-one (7.00 g, 3.30 mmol) and 1, 4-dioxane (125 mL), were added bis (pinacolato)diboron (17.00g, 6.60mmol), KOAc (8.50 g, 8.25 mmol) and Pd(dppf)Cl2 (2.50 g, 0.33 mmol). The reaction mixture was stirred at 90 oC for 12h under N2 atmosphere. After cooling to r. t. the reaction mixture was filtered. The solvent evaporated under reduced pressure then added ethyl acetate (80 mL). The precipitate was filtered to obtained black solid. Yield 70%, m.p. > 250oC. 1H NMR (300 MHz, CDCl3) delta (ppm): 8.36 (s, 1H, ArH), 8.00 (d, J = 7.60 Hz, 1H, ArH), 7.48 (d, J = 7.60 Hz, 1H, ArH), 7.03 (s, 1H, NH), 4.48 (s, 2H, CH2), 1.35 (s, 12H, CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Article; Ji, Dezhong; Zhang, Lingzhi; Zhu, Qihua; Bai, Ying; Wu, Yaoyao; Xu, Yungen; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 334 – 341;,
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Application of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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.

To a suspension of 5-bromoisoindoline-l,3-dione (2.73 g, 12.1 mmol) in THF (20 mL) was added Borane-THF complex (1 M, 48 mL). The reaction was heated at reflux overnight, then cooled to 0 C, and treated with MeOH (30 mL), followed by 2 M HCI (30 mL). The mixture was heated at reflux for 2 h, then cooled to rt and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and H20 (50 mL). The separated aqueous phase was washed with DCM (50 mL x 2), then adjusted to pH 11 with 1 M NaOH (6 mL), and extracted with DCM (80 mL x 4). The combined organic phases were dried over anhydrous a2S04, filtered and concentrated in vacuo to give the crude product as dark brown oil (1.3 g, 54%), which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 198.0 [M + H]+.

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

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, 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 20780-72-7, SDS of cas: 20780-72-7

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2¡¤NH2-H2O ( 35 percent) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink 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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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Adding a certain compound to certain chemical reactions, such as: 391-12-8, name is 7-(Trifluoromethyl)isatin, 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 391-12-8, Product Details of 391-12-8

General procedure: Isatin (0.5 g, 3.34 mmol) was added into a stirred solution ofKOH (0.56 g, 10.02 mmol) in ethanol 10 ml at 80 C. The reactionmixture was stirred at 0 C for 24 h. The mixture was added to50 g ice water. The pH was adjusted by the solution of 2 N HCl to4?5. The mixture was cooled overnight and filtered. The residuewas recrystallized by the mixture of petroleum/ethyl acetate(5:1). Compound 4 (0.8 g) was obtained and the yield was 96.87percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-(Trifluoromethyl)isatin, and friends who are interested can also refer to it.

Reference:
Article; Liao, Chen; Liu, Yan; Liu, Chunxia; Zhou, Jiaqi; Li, Huilan; Wang, Nasi; Li, Jieming; Liu, Taiyu; Ghaleb, Hesham; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 845 – 854;,
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Electric Literature of 104618-32-8, These common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)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.

Example 8 3-Amino-6-methoxycarbonyl-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (0.37 g) with 4-ethoxycarbonylphenylhydrazine hydrochloride (0.33 g), and subsequent deprotection by the method described in example 3, gave the title compound free base. This was converted to the oxalate salt (0.11 g), mp 230-240C dec.

The synthetic route of 104618-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
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Indoline | C8H9N – PubChem

Reference of 169037-23-4, 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. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-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 133-(1 ,4′-bipiperidin-1 ‘-ylmethyl)-//-(1 -phenylcvclopropyl)-6-r(trifluoromethyl)oxyl-2-r3- (trifluorometh l)phenyll-4-quinolinecarboxamide3-methyl-6-r(trifluoromethyl)oxyl-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxylic acidTo a suspension of 5-[(trifluoromethyl)oxy]-1 /-/-indole-2,3-dione (5.0 g, 21 .63 mmol) in ethanol (50 mL) was added a solution of potassium hydroxide (7.28 g, 130 mmol) in water (20.00 mL) slowly. 1 -[3-(Trifluoromethyl)phenyl]-1 -propanone was added (4.37 g, 21.63 mmol) and the mixture was heated to reflux for 1 h. The ethanol was removed under reduced pressure and the residue was dissolved in water and washed with diethyl ether. The aqueous mixture was chilled and adjusted to pH 3 with concentrated HCI. The solid was collected by filtration, washed with H20, and air dried to afford 3-methyl-6- [(trifluoromethyl)oxy]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (8.5 g, 95% yield). MS (m/z) 416.1 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

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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Indoline | C8H9N – PubChem

Synthetic Route of 41663-84-7, 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 41663-84-7 as follows.

EXAMPLE 7 A first 2-l oil-jacketed reactor with a bottom valve was equipped with a mechanical stirrer, Dean-Stark trap topped with a reflux condenser, and nitrogen supply means. It was charged with 260.8 g (1.265 moles) of 4-nitro-N-methylphthalimide, 473 ml of ODCB and 25 g (95 mmol) of HEGCl (dried from a brine solution as described hereinabove). The solution was heated to reflux and 100 ml of ODCB was removed with a nitrogen sweep. A second, similarly equipped 2-l oil-jacketed reactor was placed under the first reactor and charged with 124 g (1.265 mole) of potassium acetate and 293 ml of ODCB. This mixture was heated and ODCB removed in the same way. The contents of the first reactor were transferred over 10 minutes, with stirring, to the second via a transfer tube, with maintenance of the temperature at 1 85 C. Refluxing was observed and colorless oxides of nitrogen evolved; they turned brown upon exposure to air. Heating and stirring were continued for 6 hours, after which the mixture was allowed to cool and solids were removed over 4 hours by suction filtration through a fritted funnel. The solids so removed were washed twice with 100-ml portions of water and vacuum dried at 140 C., yielding the desired 4,4′-oxybis(N-methylphthalimide) in 71% yield.

According to the analysis of related databases, 41663-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; General Electric Company; US6028203; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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 15362-40-0, Computed Properties of C14H9Cl2NO

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
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These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)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. COA of Formula: C9H6BrNO2

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Adding a certain compound to certain chemical reactions, such as: 147149-84-6, name is 4-Bromo-5-methylindoline-2,3-dione, 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 147149-84-6, Product Details of 147149-84-6

A mixture of 3N NaOH (80 ml, 79.15 mmol) and 4-bromo-5-methyl-lH-indole-2,3-dione (19 g, 79.15 mmol) was heated at 80C. To the solution was added hydrogen peroxide (18 ml, 176.22 mmol) slowly and the mixture was stirred for 1 hour and the mixture cooled to 5C then acidified to pH5 with concentrated HCI. The solution was evaporated to dryness and methanol (100 ml) then added. The mixture was filtered and the filtrate was evaporated to yield 6-amino-2-bromo-3-methylbenzoic acid (18 g, 99%) as brown solid. 1H NMR (400 MHz, DMSO, 30C) 2.21 (3H, s), 6.71 (1H, d), 7.07 (1H, d). Three exchangeable protons not observed m/z: ES+ [M+H]+ = 230.

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, 4-Bromo-5-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; KETTLE, Jason, Grant; BAGAL, Sharanjeet, Kaur; EATHERTON, Andrew, John; FILLERY, Shaun, Michael; ROBB, Graeme, Richard; LAMONT, Scott, Gibson; KEMMITT, Paul, David; GOLDBERG, Frederick, Woolf; (158 pag.)WO2019/215203; (2019); A1;,
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