Author: tianli

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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., 1074-82-4

To a solution of l-bromopropan-2-one (5 g, 36.5 mmol, 1.0 equiv) in ACN (50 mL) was added potassium l,3-dioxoisoindolin-2-ide (7.5 g, 40.5 mmol, 1.11 equiv.). The mixture was stirred at 80 C for 2 h, cooled to rt, and quenched with water (50 mL), and extracted with DCM (50 mL) twice. The combined organic layer was washed with brine (100 mL), dried over Na2S04, concentrated under reduced pressure, and purified by silica gel column chromatography using PE/EA (1/2) as eluent to afford 6.6 g of 2-(2- oxopropyl)isoindoline-l,3-dione (Intermediate 64-1) as a yellow solid. LRMS (ES) m/z 204 (M+H).

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Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
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324-03-8, 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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one (10 g, 38.6 mmol) was added in toluene (250 ml_). The mixture was cooled down to 0C and NaH 60% in mineral oil (2.315 g, 57.9 mmol) was added portionwise. The reaction mixture was allowed to warm up and stir at RT for 30 min. Dimethyl sulfate (5.53 ml_, 57.9 mmol) was added and the reaction mixture was heated up and stirred at 60C for 3 hr, cooled down to 5C and quenched with water (50 ml_). The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHC03 solution and brine. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure to afford the title product (1 1.3 g, 36.0 mmol, 93% yield) as brown solid. Rt = 1.03 min (UPLC-MS); ESI-MS = 274.2 [M+1]+ (UPLC-MS); 1H NMR (400 MHz, DMSO-d6) d ppm 1.29 (s, 12 H) 3.13 (s, 3 H) 3.55 (s, 2 H) 6.99 (d, J= 7.82 Hz, 1 H) 7.53 (s, 1 H) 7.61 (d, J= 7.95 Hz, 1 H).

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Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
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1168150-46-6, The chemical industry reduces the impact on the environment during synthesis 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The chemical industry reduces the impact on the environment during synthesis (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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3484-35-3, Adding a certain compound to certain chemical reactions, such as: 3484-35-3, name is 5-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 3484-35-3.

General procedure: To a solution of hydrazide 4 (10 mmol, 0.36 g) in ethanol (20 mL), the appropriate isatin (10 mmol) was added followed by a catalytic amount of acetic acid (0.5 mL) then the mixture was refluxed for 1 h. The formed precipitate was filtered off, washed with hot ethanol and recrystallized from DMF/ EtOH to give the targeted compounds 5a-d. 4.1.3.4 4-(3-(2-(5-Methyl-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide (5d) Yellow powder, 77% yield; mp > 300 C. IR (KBr) numax/cm-1 3344-3215 (NH2, NH), 1714, 1685 (C=O), 1517 (C=N), 1340, 1166 (SO2). 1H NMR (DMSO-d6, 300 MHz) delta 2.30 (s, 3H, CH3), 6.83 (d, 1H, J = 7.9 Hz, H-7 of isatin), 7.17 (d, 1H, J = 7.9 Hz, H-6 of isatin), 7.26 (s, 1H, H-4 of pyrazole), 7.27-7.35 (m, 5H, Ar-H), 7.49 (s, 2H, SO2NH2, D2O exchangeable), 7.57 (d, 2H, J = 8.1 Hz, Ar-H), 7.65 (d, 1H, J = 7.8 Hz, H-4 isatin), 7.91 (d, 2H, J = 8.7 Hz, Ar-H), 10.81, 11.22 (2s, 1H, NH isatin, D2O exchangeable), 11.54, 14.13 (2s, 1H, NH hydrazone, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz) delta 20.48 (CH3), 109.07, 110.87, 119.88, 121.29, 125.37, 125.90, 126.69, 128.54, 129.21, 131.68, 132.13, 138.08, 140.28, 141.34, 143.91, 145.43, 157.50, 162.61. MS m/z [%] 500 [M+, 5.60], 222 [100]. Anal. Calcd for C25H20N6O4S (500.53): C, 59.99; H, 4.03; N, 16.79; S, 6.41. Found: C, 60.23; H, 4.11; N, 16.93; S, 6.46.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ibrahim, Hany S.; Abou-Seri, Sahar M.; Tanc, Muhammet; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 583 – 593;,
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59-48-3, 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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (1.3 g) in 20 mL of acetonitrile was cooled to -10 C. and 2.0 g of N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of 5-bromo-2-oxindole. 1H NMR (360 MHz, DMSO-d6) delta10.44 (s, br, 1H, NH-1), 7.32-7.36 (m, 2H), 6.76 (d, J=8.5 Hz, 1H, H-7), 3.5 (s, 2H, CH2). MS m/z 212.1 and 214.1 [M and M+2]+.

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Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
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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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 99365-40-9

a) 6-Bromo-1,3,3-trimethylindolin-2-oneUnder an argon atmosphere NaH (60 % on mineral oil, 7.32 g, 183 mmol) was suspended in dry THF (45 ml). A suspension of 6-bromoindolin-2-one (10 g, 45.7 mmol) in dry THF (108 ml) was added in portions during 10 minutes while temperature was kept below 27 C. The reaction mixture was warmed to 25 C and Mel (11.4 ml, 183 mmol) was added dropwise during 1 hour while the internal temperature was carefully kept between 24 and 27 C. The reaction mixturewas stirred at room temperature for 18 hours. Saturated aqueous NT-L1C1 solution (20 ml) was carefully added at 10-15 C. The mixture was diluted with EtOAc, H20 and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc, the organic layers were washed with saturated aqueous NaHCO3 solution, combined and dried with Na2504. The solvent was evaporated and the residue was purified by silica gel chromatography using heptane / ethylacetate as eluent. The title compound was obtained as light red solid (7.0 g). Mixed fractions were purified again by preparative HPLC yielding further 3.1 g of the title compound.MS ESI (m/z): 254.1, 256.2 [(M+H)i.1H NMR (CDC13, 300 MHz): oe = 7.19 (dd, J=1.5, 7.8 Hz, 1H), 7.06 (d, J=7.9 Hz, 1H), 6.99 (d, J=1.6 Hz, 1H), 3.19 (s, 3H), 1.35 (s, 6H).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
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99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Four microwave vials were loaded as follows: 6-bromoindolin-2-one(500 mg, 2.36 mmol), bis(pinacolato)diboron (898 mg, 3.54 mmol),potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)C12CH2C12 (96.0mg, 0.118 mmol) were dissolved in DME (17 mL). The reaction was heated at 80 C overnight. The content of the four vials was then combined, concentrated and purified bycolumn chromatography (CyHex/EtOAc) to afford the title compound as a white solid (2.27 g, 75%, purity 80%). IH NMR (500 MHz, CDCI3) ppm = 8.57 (bs, IH), 7.48 (d, J7.3, IH), 7.31 (5, 1H), 7.23 (d, J=7.3, IH), 3.55 (s, 2H), 1.33 (s, 12H); LC – MS (ESI, mlz) Rt = 2.75 mm – 260 (M+H) (H PLC method E).

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Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
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Some common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, molecular formula is C14H11NO, 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. 3335-98-6

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3¡Á30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3335-98-6, its application will become more common.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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2913-97-5, Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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 2913-97-5.

Example 28B; tert-butyl (2S, 3S)-2-{[2-(1, 3-dioXo-1, 3-dihydro-2H-isoindol-2-yl) ethyl] amino}-3- methylpentanoate; To a solution of Example 28A (12.1 g) in methanol (20 mL) was added L-isoleucine tert-butyl ester hydrochloride (13.0 g, 58 mmol), sodium cyanoborohydride (7.3 g, 116 mmol), and acetic acid (2mL). The resulting solution was stirred for 3 hrs at 25¡ãC and the methanol removed under vacuum, dichloromethane (500 mL) added, and the solution washed with aqueous NaHC03 (2 x 300 mL). The organic layer was concentrated to give 12.9 g of the title compound.

According to the analysis of related databases, 2913-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/61487; (2005); A1;,
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Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. 675109-26-9

(6-( 1 – (and 2-)(4-methoxybenzyl)-2H-tetrazol-5 -yl)-4′-methyl-5-sulfamoyl- [ 1 , 1 ‘- biphenyl]-3-yl)boronic acid (40 mg, 0.083 mmol) and 6-bromoisoindolin-l-one (19.47 mg, 0.092 mmol) was suspended in ethanol (835 mu) and potassium phosphate tribasic (250 mu, 0.250 mmol). The reaction mixture was sparged with 2 for 5 min. 1 , l’-bis(di-tert- butylphosphino)ferrocene palladium dichloride (5.44 mg, 8.35 muiotaetaomicron) was added and the reaction mixture micro waved at 1 10C for 90 min. The crude reaction mixture was diluted with EtOAc and water. The aqueous phase was extract with EtOAc (x2), then the combined extracts were washed with brine, dried over Na2S04, filtered, and concentrated. The reaction mixture was purified by reverse phase HPLC on a Cis column and then eluted with 10% to 100% MeCN in water. The major UV active material was lyopholized to provide a white solid that was utilized directly in the deprotection. LC-MS: calculated for C3oH26N604S 566.2; observed m/e: 467.5 (M+H)+. The resulting solid was dissolved in TFA and heated to 45C overnight, then concentrated. The residue was purified by reverse phase HPLC on a Cis column eluted with 0% to 80% MeCN in water. The major UV active material was lyopholized to provide 4′-methyl-5- (l-oxoisoindolin-5-yl)-2-(2H-tetrazol-5-yl)-[l, l’-biphenyl]-3-sulfonamide. LC-MS: calculated for C22H18N603S 446.1 ; observed m/e: 447.4 (M+H)+; 1H NMR delta (ppm) (DMSO): 8.72 (s, 1H), 8.44 (s, 1H), 8.16 (s, 1H), 8.12 (d, 1H), 8.05 (s, 1H), 7.77 (d, 1H), 7.60 (s, 2H), 7.11-7.05 (m, 4H), 4.48 (s, 2H), 2.27 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-26-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
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