Tag: M.W=200-300

Application of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of compound 5-bromoisoindolin-1-one(200 mg, 0.94 mmol, 1.0 eq), 1-methyl-3-(4,4,5,5-tetram-ethyl-i ,3,2-dioxaborolan-2-yl)- 1H-pyrazole (215 mg, 1.04mmol, 1.1 eq), cesium carbonate (922 mg, 2.83 mmol, 1.2eq), and Pd(dppf)C12 (21 mg, 0.03 mmol) in 1,4-dioxane(15mE) and water (2 mE) was stirred at 1000 C. for 16 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (30%-100% EtOAc in PE) to give 4A (120 mg, 60% yield): ?H NMR (400 MHz, CDC13) oe 7.96 (s, 1H), 7.89 (d, J 0.8 Hz, 2H), 7.43 (d, J 2.2 Hz, 1H), 6.62 (d, J 2.3 Hz, 1H), 6.36 (s, 1H), 4.48 (s, 2H), 3.99 (s, 3H).

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-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. COA of Formula: C8H4BrNO2

5-bromo-2-ethylisoindoline-1,3-dioneTo a solution of 5-bromoisoindoline-1 ,3-dione (1 130 mg, 5 mmol) in THF (25 mL) was added iodoethane (0.606 mL, 7.50 mmol) and then slowly was added NaH (144 mg, 6.00 mmol). The resulting reaction was stirred at RT for 22 h. To the reaction mixture was added DMF (2 mL) then stirred at RT for 23 h. To the reaction mixture was added more DMF (3 mL) then was stirred at RT for 120 h. The reaction mixture was diluted with H20 (20 mL), acidified with HCI (1 mL, 1.0 N), extracted with EtOAc (3 x 20 mL), washed with brine (20 mL), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product 5-bromo-2-ethylisoindoline-1 ,3-dione (899.7 mg, 3.54 mmol, 70.8 % yield). LC-MS mlz 254.1 (M+H)+, 0.90 min (ret. time).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); 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: Isatin 1 (147.1 mg, 1 mmol), (E)-1-phenylpent-2-ene-1,4-dione (2a, 348.4 mg, 2 mmol), and thiourea I (57 mg, 0.1 mmol) were cooled to -20 °C, dissolved in toluene (3 mL), and the mixture was stirred at -20 °C for 24 h. The progress of the reaction was monitored by TLC and NMR spectroscopy. The product was isolated by direct column chromatography on silica gel (CH2Cl2/EtOAc 95:5 to 85:15)

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; Trubitson, Dmitri; ?ari, Sergei; Kaabel, Sandra; Kudrjashova, Marina; Kriis, Kadri; Jaerving, Ivar; Pehk, Tonis; Kanger, Tonis; Synthesis; vol. 50; 2; (2018); p. 314 – 322;,
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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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 104618-31-7

To a solution of 1.534 g (6.26 mmol) of 2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione in 60 mL THF was added 0.553 g (13.8) NaH (60% in oil) and reaction mixture stirred under N2 until gas formation ceased. The mixture was cooled to 0 C. and 3.56 g (25.1 mmol) MeI was added and the reaction was stirred at 25 C. for 24 hours. The mixture was then poured into 180 mL sat. NH4Cl(aq) and extracted 3 times with DCM. The organic layers were dried over Na2SO4, concentrated and then purified via chromatography (50% EtOAc/Hex) to give 908 mg of 2-(4-Methoxy-cyclohexyl)-isoindole-1,3-dione (48.3% yield, LCMS (m/z): M+H=301.1). That was dissolved in 40 mL EtOH and 324 mg (8.76 mmol) Hydrazine was added. The reaction mixture was stirred at 65 C. for 3 hours. By the end of the 3 hours the solution was mostly white solid and a little liquid. The reaction was filtered and washed 3 times with 30 mL MeOH and concentrated to give 450 mg of crude product of 4-Methoxy-cyclohexylamine (ca. 100% yield). LCMS (m/z): M+H=130.2.

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 104618-31-7.

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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Synthetic Route of 2058-72-2,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.

General procedure: To a mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
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Electric Literature of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

2-((4-Methyl-2.5-dioxoimidazolidin-4-yl)methylcarbamoyl)benzoic acid [0180] Phthalimido acetone (27-1) (14.2 g, 70 mmol, 1 eq.), ammonium carbonate (23.5 g, 245 mmol, 3.5 eq), potassium cyanide (6.8 g, 105 mmol, 1.5 eq.) in EtOH (70 mL) and H2O (70 niL) were heated at 75 0C for 18 h in a sealed tube. The reaction mixture was cooled to room temperature and the volatiles were evaporated in vacuo. The reaction mixture was partitioned between ethyl acetate (150 mL) and H2O (100 mL). The aqueous phase was adjusted to pH 4 and extracted with more ethyl acetate (2 x 150 mL). Organic layers were combined, dried (MgStheta4) and concentrated in vacuo to yield the crude product (27-2), which was directly used in the next step. Yield: 12.33 g (61%). 1H-NMR (400 MHz, CD3OD^) delta 7.60-7.41 (m, 4H), 3.70 (d, IH), 3.56 (d, IH), 1.44 (s, 3H). LCMS – [M+H] m/z 292.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Oxopropyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVABAY PHARMACEUTICALS, INC.; JAIN, Rakesh, K.; LOW, Eddy; FRANCAVILLA, Charles; SHIAU, Timothy P.; KIM, Bum; NAIR, Satheesh, K.; WO2010/54009; (2010); A1;,
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Reference of 4702-13-0, These common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, 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.

7-b: 1-Bromo-3-phthalimide acetone 2-Phthalimide acetic acid 2.05 g (10.0 mmol), 10 mL of thionyl chloride,Placed in 50mL reaction flask, reflux to the remaining raw materials, vacuum drying, in a brown oil, add 2mL toluene. 15 mL of 50% by weight aqueous solution of KOH was added to 40 mL of diethyl ether, and 6.00 g (33. Mmol) of nitrosourea was slowly added in portions under ice-cooling. After addition, shaking was continued for 10 minutes. , & Lt;And dried for 2 hours in the form of flake KOH to obtain a solution of diazomethane in diethyl ether.The above-mentioned diazomethane-containing ether solution was placed in a 100 mL reaction flask and placed in an ice bath. 2 mL of a toluene solution containing the above oil was slowly added dropwise. The reaction was complete, filtered, rinsed with diethyl ether and the resulting solid spare. The solid was dissolved in 20 mL of tetrahydrofuran, and 2 mL of a 40 wt% aqueous solution of HBr was added dropwise to the reaction mixture, and the mixture was dried under reduced pressure. Add 100mL ethyl acetate, placed in a separatory funnel, respectively, saturated NaHC03, water, saturated NaCl solution, dried anhydrous Mg2S04. Dried under reduced pressure and recrystallized from 95% by weight ethanol to give 1.24 g of a white solid in 44.0% by weight yield.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Union Pharmaceutical Factory; Institute of Materia Medica, Chinese Academy ofMedical Sciences; Pan, Xiandao; Zhang, Peicheng; Yang, Yajun; Zhao, Limin; (20 pag.)CN102786464; (2016); B;,
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Application of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); 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. 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClNO4S

To a slurry of 2,3-dioxomdoline-5-sulfonyl chloride (Lee, D. et al. J. Med. Chem. 2001, 44, 2015) (7,07 g, 28.8 mmol) m CH2Cl2 (288 mL) at rt was added neopentyl alcohol (7.61 g, 86.3 mmol) then pyridine (11.6 mL, 143 mmol). The reaction was stirred at rt for 22 hours, becoming a clear, oiange solution. The reaction was diluted with ILO (300 mL) and extracted with EtOAc (2 chi 600 mL). The combined organic extracts were washed with 0.1 M aqueous HCl (3 * 300 mL), saturated aqueous NaHCO3 (300 mL), and saturated aqueous NaCl (300 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound as a yellow solid (6.40 g, 92%). 1H NMR (400 MHz, CDClj): consistent; MS (ES ) m’z 315.1 (,VHH2O)

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 132898-96-5.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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: C14H13NO3

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
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