Author: Jessica.F

Synthetic Route 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 the reaction vessel, 6-bromoisatin (10.0 g, 22 mmol) and 1N aqueous NaOH solution (48 mL) were added and the mixture was heated to 50C and stirred for 1 hour. The reaction solution was cooled to 0C, and a mixture of sodium nitrite (3.0 g, 22 mmol) and water (11 mL) was added slowly. Water (90 mL) and sulfuric acid (4.6 mL) were slowly added to the mixture at the same temperature and stirred. To the reaction mixture was added a mixture of tin chloride dihydrate (24.0 g, 53 mmol) and hydrochloric acid (40 mL) at 0 C, and the mixture was stirred at room temperature. The resulting solid was filtered, washed with water and dried to give the desired compound (8.53 g, 80% yield) as a yellow solid.

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

Reference:
Patent; Korea Institute of Science and Technology; Sim Tae-bo; Noh Eun-ju; Yang Han-yong; (33 pag.)KR101936851; (2019); B1;,
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Electric Literature of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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 tert-butyl 3-amino-4-methylphenylcarbamate (0.667 g, 3 mmol), 2-(l,3-dioxoisoindolin-2-yl)acetyl chloride (0.671 g, 3.00 mmol) in DCM (10 mL) was added diisopropylethylamine (1.048 mL, 6.00 mmol). After stirring 25 C for 15 h, saturated aqueous sodium chloride (25 mL) was added and extracted with ethyl acetate (3 x 25 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated. The crude product was purified by silica gel chromatography (100% ethyl acetate) to give the title compound as a white solid (1.15 g, 2.81 mmol, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta 9.70 (s, IH), 9.29 (s, IH), 7.91 – 7.99 (m, 2H), 7.83 – 7.91 (m, 2H), 7.56 (s, IH), 7.13 (d, J= 8.20 Hz, IH), 7.07 (d, J- 8.20 Hz, IH), 4.45 (s, 2H), 2.11 (s, 3H), 1.45 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
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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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromoisatin

To a solution of 4-bromoisatin 30 (200 mg, 0.88 mmol) in THF/water (3:1, 3 mL) was added potassium 3-thienyltrifluoroborate (235 mg, 1.24 mmol) and K3PO4 (675 mg, 3.19 mmol) followed by Pd(PPh3)2Cl2 (62 mg, 0.09 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 ¡ãC. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL) and filtered through Celite?. The organic solution was washed with brine (10 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 30-40 ¡ãC petrol/acetone, 4:1) to afford the title compound (43) as an orange solid (120 mg, 59percent); mp 213-216 ¡ãC; numax (solid) 3098, 2927, 1727, 1584; deltaH (500 MHz, DMSO-d6) 6.85 (1H, dd, J = 7.9, 0.6 Hz, C(7)H), 7.20 (1H, dd, J = 7.9, 0.6 Hz, C(5)H), 7.50 (1H, dd, J = 4.9, 1.3 Hz, C(4′)H), 7.58 (1H, app t, J = 7.9 Hz, C(6)H), 7.62 (1H, dd, J = 4.9, 2.9 Hz, C(5′)H), 8.07 (1H, dd, J = 2.9, 1.3 Hz, C(2′)H), 11.13 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 110.8, 113.9, 123.8, 125.6, 126.3, 128.4, 135.8, 137.2, 138.0, 151.6, 158.9, 183.0; m/z (ESI-) 228 ([M-H]-, 100percent); HRMS (ESI-) C12H6N4O2S- ([M-H]-) requires 228.0125; found 228.0127.

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
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Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-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 61-70-1, SDS of cas: 61-70-1

No. A1-173: 1-(3-Bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (0127) (0128) Together, 1-methyl-1,3-dihydro-2H-indol-2-one (2.00 g, 14 mmol) and 1,2-dibromoethane (3.83 g, 20 mmol) were dissolved in abs. N,N-dimethylformamide (15 ml), sodium hydride (1.68 g, 42 mmol, 60% strength dispersion) was then added carefully a little at a time at a temperature of 10-15 C. and the mixture was stirred for another one and a half hours. Methanol and aqueous ammonium chloride solution were then added to the reaction mixture, and the aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2500 mg, 92% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.25 (m, 1H), 7.03 (m, 1H), 6.91 (d, 1H), 6.83 (d, 1H), 3.30 (s, 3H), 1.73 (m, 2H), 1.52 (m, 2H). 1?-Methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2.50 g, 13 mmol) was added to glacial acetic acid (23 ml), and fuming nitric acid (4 ml) was then added slowly and carefully. The resulting reaction mixture was stirred at room temperature for 30 minutes and then slowly diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium carbonate solution and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1800 mg, 57% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.25 (dd, 1H), 7.74 (d, 1H), 6.97 (d, 1H), 3.36 (s, 3H), 1.88 (m, 2H), 1.69 (m, 2H). In the next step, 1?-methyl-5-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1.80 g, 8 mmol) and tin(II) chloride dihydrate (7.45 g, 33 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1226 mg, 79% of theory) as a colorless solid. 1H-NMR (400 MHz, CDC138, ppm) 6.71 (d, 1H), 6.60 (dd, 1H), 6.25 (d, 1H), 3.52 (br. s, 2H, NH), 3.24 (t, 2H), 1.71 (m, 2H), 1.43 (m, 2H). In a round-bottom flask under argon, 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (130 mg, 1.0 equiv.) and (3-bromophenyl)methanesulfonyl chloride (261 mg, 1.4 equiv.) were dissolved together in abs. acetonitrile, pyridine (0.11 ml, 2.0 equiv.) and dimethyl sulfoxide (0.03 ml, 0.60 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1-(3-bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (235 mg, 81% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (m, 1H), 7.39 (m, 1H), 7.29 (m, 1H), 7.24 (m, 1H), 7.04 (m, 1H), 6.87 (d, 1H), 6.65 (d, 1H), 6.26 (s, 1H, NH), 4.13 (s, 2H), 3.30 (s, 3H), 1.78 (m, 2H), 1.54 (m, 2H). 13C-NMR (150 MHz, CDCl3 delta, ppm) 176.8, 141.7, 133.7, 132.6, 132.1, 130.8, 130.4, 129.5, 122.6, 120.8, 113.3, 108.3, 56.8, 27.4, 26.7, 19.7.

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:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); A1;,
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Reference of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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-aminophthalimide (0.62 mmol), 2,6-dichlorophenylisocyanate (0.62 mmol), and DMF (cat.) in toluene (3 mL) was heated at 105 C for 19 h. The reaction mixture was concentrated and the crudematerial was purified via preparative HPLC to give compound 117 in 1% yield. ?H NMR (400MHz, DMSO-d6) 11.15 (s, 1H), 9.78 (s, 1H), 8.60 (s, 1H), 8.05 (t, J 1.2 Hz, 1H), 7.73 (d, J1.2 Hz, 2H), 7.57 (d, J= 8.1 Hz, 2H), 7.36 (t, J= 8.1 Hz, 1H). ?3C NIVII{ (101 1VIHz, DMSO)169.63, 169.49, 152.71, 146.11, 134.78, 134.62, 133.35, 129.33, 129.00, 125.49, 124.55, 122.71,111.96.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
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39755-95-8, name is 5-Methoxyisatin, 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. HPLC of Formula: C9H7NO3

General procedure: A mixture of malononitrile (1 mmol), isatin (1 mmol), dicarbonyl (1 mmol), PEGOSO3H(0.1 mmol), and water (2 mL) was stirred under reflux for the appropriate time (shown in Tables 3, 4). After completion of the reaction, the reaction mixture was filtered and the residue was washed with ethanol. The crude solid product was recrystallized from EtOH to afforded the pure products in high purity and yield.Assignment of the structures of the products was based on their 1H NMR, 13C NMR,and IR spectra.

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nasseri; Zakerinasab; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5261 – 5270;,
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Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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 5332-26-3, Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

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).

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; 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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Application of 20870-78-4, 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. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-(4,4,5,5-Tetramethyl-l,3,2-dioxaboroIan-2-yl)-l,3-dihydroindol-2-one; A mixture of 5-bromo-2,3-dihydroindol-2-one (500 mg), bis(pinacolato)diboron (899 mg) and potassium acetate (695 mg) in DMF (20 mL) was degassed for 5 minutes. 1,1′- 5 Bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (78 mg) was added to the mixture and the reaction was heated to 8O0C and left to stir for 3 hours. The reaction mixture was filtered through celite and concentrated in vacuo. The residue was suspended in water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The organics were dried (MgSO4), filtered and concentrated in vacuo to give the desired 0 material as a brown solid. (611 mg). Mass Spectrum; M+H+MeCN+ 301.NMR Spectrum: 1H NMR (DMSOd6) deltal.28 (12H, s), 3.47 (2H, s), 6.82 – 6.84 (IH, d), 7.51 (2H, m), 10.52 (IH, s)

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); A1;,
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Electric Literature of 3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3¡¤Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

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

Reference:
Article; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
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Related Products of 4702-13-0, 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. 4702-13-0, name is N-Phthaloylglycine belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 4 Phthalimidoacetyl chloride A mixture of phthalimidoacetic acid (25.1 g, 0.122 mol) and thionyl chloride (50 mL) was heated for one hour under reflux. The reaction mixture was cooled and, then, concentrated under reduced pressure. The concentrate was recrystallized from dichloromethane-hexane to give 26.4 g (97%) the titled compound, which was used for the subsequent reaction 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, N-Phthaloylglycine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5834463; (1998); A;,
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