Tag: M.W=100-200

Synthetic Route of 6872-06-6, A common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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 7Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-methyl-1-(phenylsulfonyl)indolineReagents MW Reagent/raw material (g/mole) Quantity moles 2-methylindoline 133.20 1 g 7.5 mmol benzenesulfonyl chloride 176.62 1.98 g 11 mmol 2-methyl-1- 273.35 0.76 g 2.77 mmol (phenylsulfonyl)indoline 2,3- 234.66 0.5 g 2.13 mmol dihydrobenzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 0.369 g 2.77 mmol Step 1: 2-methylindoline was dissolved in 5 mL dry pyridine, and benzenesulfonyl chloride was dropped in. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When complete as determined by HPLC using the protocol in Example 1 above, as well as by LCMS, the crude reaction was poured into 100 mL cold 1M KHSO4, and extracted twice with 50 mL CH2Cl2. The organic phase was dried, evaporated and purified by CombiFlash to provide 2 grams of 100% pure product (97% yield).

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; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); 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. 25369-33-9, name is 7-Chloroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Chloroindolin-2-one

Example 54Preparation of 7-chloro-5-[Y2-((‘l S,2S)-2-[l-(5-chloropyrimidin-2-yl)piperidin-4- yli cvclopropyU ethvDaminol -1.3 -dihvdro-2H-indol-2-oneStep 1 ; 7-chloro-5-nitro-13-dihvdro-2H-indol-2-one7-chloro-1,3-dihydro-2H-indol-2-one (8.Og, 47.7 mmol) was slurried in H2SO4 (cone, 86 ml) and the mixture cooled to -45 C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at -45 C throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0 C for 1 hour. The solid was collected by filtration, triturated with cold water (2x)? and dissolved into EtOAc (1 L). This mixture was filtered, washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.

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 25369-33-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
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These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. HPLC of Formula: C9H7NO3

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ×3 mL). The DCM layer was combined and washed with brine solution (25 × 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
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Application of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-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 stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0 C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0 C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80 C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
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Synthetic Route of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(l,3-dioxoisoindolin-2-yl)acetaldehyde (product of step-3, 4.0 g, 21.15 mmol) in ethanol (40 mL), added hydroxylamine hydrochloride (2.930 g, 42.305 mmol) followed by sodium bicarbonate (3.55 g, 42.305 mmol) at room temperature and stirred at room temperature for 16 h. The solvent was stripped off, added water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with water (100 mL) followed by brine, dried over sodium sulphate and concentrated under vacuum to get the title compound (3.2 g, 74percent) as an off white solid. LCMS: m/z 204.1 [M+H] +; NMR (300 MHz, DMSO-d6) delta 11.36 (s, 1H), 7.98 – 7.78 (m, 4H), 6.83 (t, / = 3.8 Hz, 1H), 4.39 (dd, / = 3.9, 0.9 Hz, 2H).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

Example 37 Preparation of intermediate E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one To the mixture of 6-chlorooxindole (3.3 g, 20 mmol) (Crescent) and 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal (6.5 g, 26.6 mmol) in methanol (150 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (10 g, 46 mmol) dropwise. The reaction mixture was stirred at room temperature for 10 min. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (25-33% EtOAc in hexanes) to give E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one as a off white solid (Yield 3.6 g, 46%).

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, 6-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Liu, Jin-Jun; Zhang, Jing; Zhang, Zhuming; US2011/201635; (2011); A1;,
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Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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: 19155-24-9

Step 4:3,3-dimethyl-2,3-dihydro-1H-indoleUnder a nitrogen atmosphere a solution of 6.20 mL (6.20 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.00 g (6.20 mmol) 3,3-dimethyl-1,3-dihydro-indol-2-one in 50 mL THF.Then the reaction mixture was heated to 60¡ã C. for 1 h.After cooling to 0¡ã C., 3 mL ice water were slowly added dropwise.20 g sodium sulphate were added and the mixture was suction filtered.The solution was evaporated down i. vac.Yield: 0.80 g (88percent of theory)ESI-MS: m/z=148 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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Synthetic Route of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: 4.4.18 (Z)-5-methoxy-3-((2-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazol-6-yl)methylene)indolin-2-one (5r) Compound 5r was prepared according to the method described for compound 5a, employing aldehyde 11e (156 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81 mg, 0.5 mmol) to obtain the pure product 5r as a yellow solid (134 mg, 59%); mp: 168-166 C; IR (KBr): 3425, 3174, 2354, 1690, 1640, 1575, 1488, 1435, 1280, 1120, 1032, 992, 846, 742 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.34 (bs, 1H), 7.89 (s, 1H), 7.77 (s, 1H), 7.66 (d, J = 8.1 Hz, 1H), 7.58 (s, 1H), 7.54 (s, 2H), 7.36 (s, 1H), 6.89-6.66 (m, 2H), 3.92 (s, 6H), 3.76 (s, 3H), 3.62 (s, 3H); 13C NMR (75 MHz, CDCl3 + DMSO-d6): delta 168.9, 153.7, 153.0, 139.0, 137.3, 136.3, 128.2, 127.7, 126.2, 124.8, 121.9, 114.2, 113.8, 111.2, 111.1, 110.0, 108.9, 108.5, 103.8, 59.9, 55.8, 55.0; MS (ESI): m/z 458 [M + H]+; HRMS (ESI) calcd for C26H24O5N3 m/z 458.16992 [M + H]+; found 458.17105.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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: Compound 7 (2.1 g, 0.012 mol) and HBTU (5.0 g, 0.013 mol) were dissolved in dry DMF, in a 250 ml round bottom flask. DIPEA (6.5 ml, 0.037 mol) was added and the reaction mixtures were stirred for 30 min. L or D- phenylalanine methyl ester hydrochloride (3.0 g, 0.014 mol) or glutamic acid dimethyl ester hydrochloride (3.0 g 0.014 mol) was added and the reaction mixture was kept stirring overnight under ambient conditions. Reaction monitoring by TLC was performed on silica gel plates using CHCl3:MeOH 9:1 as eluent. Saturated NaHCO3 solution (150 ml) was added to the mixture and the precipitate was filtered, washed with saturated NaHCO3 solution and water. The crude product was purified by column chromatography CHCl3:MeOH (95:5) to give the product as white to off-white solid.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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Adding a certain compound to certain chemical reactions, such as: 100510-65-4, name is 6-Amino-3,3-dimethylindolin-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 100510-65-4, name: 6-Amino-3,3-dimethylindolin-2-one

Example No.11: 6-(4-(Cyclopropylamino)furo[3,2-i/|pyrimidin-2-ylamino)-3,3- dimethylindolin-2-oneTo a flask was added 2-chloro-A^-cyclopropylfuro[3,2-i/]pyrimidin-4-amine (0.45 g, 2.14 mmol, Example No.3, Step C), 6-amino-3,3-dimethylindolin-2-one (0.378 g, 2.14 mmol, Astatech), K2C03 (0.89 g, 6.44 mmol) and i-AmOH (5 mL). To the mixture was added Pd2dba3 (0.1 18 g, 0.129 mmol) and X-Phos (0.123 g, 0.258 mmol). The mixture was heated to about 100 C and stirred for about 15 h. The mixture was filtered and the filtrate was directly purified by column chromatography eluting with 0 to 70% of 10% MeOH/DCM (containing 2M 1.5% NH3 in EtOH) and DCM (25 g silica gel)). The material was then dried in a vacuum oven at about 65 C for about 48 h. The solid was then suspended in Et20 (5 mL), sonicated for 2 min and filtered. The solid was dried in a vacuum oven at about 80 C for about 16 h to give 6-(4- (cyclopropylamino)furo[3,2-ii|pyrimidin-2-ylamino)-3,3-dimethylindolin-2-one (0.195 g, 26%o): LC/MS (Table 2, Method c) R, = 1.81 min.; MS m/z: 350 (M+H)+. Syk IC50 = A

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, 6-Amino-3,3-dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
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