Tag: M.W=200-300

Application of 3339-73-9,Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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 4 (0.3 g, 1.37 mmol) in CH2Cl2 (10 mL) was added thionyl chloride (0.12 mL, 1.6 mmol). The resulting mixture was stirred at reflux for 5 h. After cooling to rt, the solvent and excess thionyl chloride were removed by evaporation to give a white solid (0.22 g) in 67% yield; 1H NMR (400 MHz, CDCl3) delta 7.87 (m, 2H), 7.74 (m, 2H), 4.04 (m, 2H), 3.35 (m, 2H); 13C NMR (100 MHz, CDCl3) delta 168.0, 166.2, 134.2, 123.5, 33.9, 33.0; mp 148-150?C. The product was used in the next step without further purification.

The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Peng; Jorgensen, Trine Nygaard; Loland, Claus J.; Newman, Amy Hauck; Bioorganic and Medicinal Chemistry Letters; vol. 23; 1; (2013); p. 323 – 326;,
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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 552330-86-6 as follows. COA of Formula: C8H6BrNO

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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Reference of 41663-84-7, 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. 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 To a reaction vessel containing dimethylacetamide (25 ml) were added 4-nitro-N-methylphthalimide (0.51 g, 0.00248 mol), biphenyl (0.21 g, 0.00139 mol), sodium hydrogen sulfide (0.14 g, 0.00125 mol) and triethylamine (0.2 ml, 0.0014 mol). The reaction was allowed to proceed at 70 C. for 24 hours. Samples of the reaction mixture were taken and examined by HPLC. A yield of 19.6% 4,4′-bis(N-methylphthalimide)sulfide was indicated. The isolated yield was 18% (0.08 g).

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, 2-Methyl-5-nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; General Electric Company; US4625037; (1986); A;,
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Synthetic Route of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step-1: tert-butyl 5-((2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (0.2 g 0.5790 mmol, 1.0 eq) in (5.0 mL) of toluene was added m-CPBA (0.280 g, 1.158 mmol, 2 eq) and allowed to stir at rt for 30 min. followed by addition of tert-butyl 5-aminoisoindoline-2-carboxylate (0.176 g, 0.7527 mmol, 1.3 eq) and DIPEA (0.3 ml 1.737 mmol, 3.0 eq) and allowed to stir at rt for overnight. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2*20 mL). The combined organic layers were washed with water (30 mL), brine (30 mL), dried over Na2SO4, concentrated and purified by combi flash [silica gel-100-200 mesh; elution 0-35% EtOAc in Hexane] to afford the desired compound, tert-butyl 5-((2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (0.100 g, 49.52%) as white 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, tert-Butyl 5-aminoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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Related Products of 20780-72-7, 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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a general procedure, a mixture of 4-chloroindoline-2,3-dione(4.4 mmol), K2CO3 (1.8 g), P-chlorobenzyl bromide (1.1 g) in DMF(10 mL) was stirred at room temperature for 4 h under argon. Thenthe reaction was quenched by adding excess ice-water and stirredfor 30 min. The suspensionwas filtered and the residuewas dried toafford 4-chloro-1-(4-chlorobenzyl)indoline-2,3-dione (1.34 g, 90percent)as a red solid without further purification. This was directly used in the next step; NH2OHHCl (1.5 mmol) was added to a solution of 4-chloro-1-(4-chlorobenzyl)indoline-2,3-dione (1.4 mmol) in Pyridine(5 mL) and the resulting mixture was heated to 110 C andstirred for 2 h. After cooling to room temperature, the resultingsolution was poured into aqueous HCl (1 M, 50 mL) and extractedwith EtOAc (350 mL). The combined organic layer was washedwith brine (330 mL), dried over Na2SO4, concentrated underreduced pressure and then recrystallized to produce 5a (382 mg,85percent) as a yellow solid. The derivatives 5b, 5c were preparedthrough this procedure by using 4-bromoindoline-2,3-dione and 4-iodoindoline-2,3-dione as material.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Yuyin; Pan, Guojun; Chen, Yue; Yang, Qian; Hao, Tiantian; Zhao, Lianbo; Zhao, Long; Cong, Yusheng; Diao, Aipo; Yu, Peng; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 370 – 378;,
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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. Recommanded Product: 132898-96-5

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 132898-96-5, 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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Application of 132898-96-5, A common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

The synthetic route of 132898-96-5 has been constantly updated, and we look forward to future research findings.

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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Application of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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 mixture of 6-bromoisatin (0.88 mmol) in AcOH (9 ml), Br2 (0.88 mmol) was added and the mixture was stirred for 48 h at reflux. After this time the reaction was cooled at 0 C, and the solid residue was paper filtered off, washed with AcOH and dried in the oven. The crude product was then recrystallized from AcOH to give the pure orange coloured product 1, 57%; mp >270 C with decomposition. 1H NMR, 300 MHz, DMSO-d6 delta = 7.23 (1H, s, H7); 7.82 (1H, s, C4), 11.22 (1H, brs, NH). 13C NMR, 75 MHz, DMSO-d6 delta = 117.40, 117.64, 119.61, 129.33, 133.81, 150.67, 159.83, 183.12.

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Article; Mollica, Adriano; Stefanucci, Azzurra; Feliciani, Federica; Lucente, Gino; Pinnen, Francesco; Tetrahedron Letters; vol. 52; 20; (2011); p. 2583 – 2585;,
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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-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 2058-72-2, Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

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; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
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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. HPLC of Formula: C9H6BrNO2

General procedure: A mixture of corresponding compound 1(0.5 mmol), isatin 3 (0.5 mmol), and sarcosine (0.5 mmol) in acetonitrile (40 mL) (for 1a-c) or in amixture of acetonitrile (30 mL) and chloroform (10 ml) (for 1d-f) was refluxed with stirring for 36 or 72 h for starting compounds 1a-c and 1d-f, respectively. Then the reaction mixture was cooled to room temperature, the precipitate of compounds 4a-e,j,o was filtered off and washed with acetonitrile and water. The reaction mixture of compounds 4f-i,k-n,p-t was concentrated on a rotary evaporator to half of an original volume. After cooling, the precipitate was filtered off and washed with water. Recrystallization from acetonitrile or methanol (4n) gave dispirocompounds 4a-t.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-72-2, its application will become more common.

Reference:
Article; Izmest’ev, Alexei N.; Gazieva, Galina A.; Sigay, Natalya V.; Serkov, Sergei A.; Karnoukhova, Valentina A.; Kachala, Vadim V.; Shashkov, Alexander S.; Zanin, Igor E.; Kravchenko, Angelina N.; Makhova, Nina N.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2240 – 2249;,
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