Tag: M.W=200-300

Electric Literature of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
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Reference of 435273-55-5,Some common heterocyclic compound, 435273-55-5, name is 4-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

2-methyl-l-oxoisoindoline-4-carbaldehyde: To a solution of 4-bromo-2- methylisoindolin-l-one (200mg, 0.89 mmol) in THF (3 mL), n-BuLi (0.78 mL, 1.95 mmol) was added to the solution at -78 C. After 30 minutes, DMF (0.273 mL, 3.57 mmol) was added to the solution. After 1 hour, the reaction was warmed up. Diluted with EtOAc and washed with brine. The organic layer was dried over sodium sulfate, and concentrated. The product was purified by chromatography on silica gel (eluent: EtOAc/hexanes) to yield the product after lyophilization from water / MeCN.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-Hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (604 pag.)WO2017/7689; (2017); A1;,
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Related Products of 41663-84-7, These common heterocyclic compound, 41663-84-7, name is 2-Methyl-5-nitroisoindoline-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.

EXAMPLE 6 To a reaction vessel were added 4-nitro-N-methylphthalimide (0.51 g, 0.00248 mol), sodium hydrogen sulfide (0.07 g, 0.00125 mol), biphenyl (0.204 g, 0.00132 mol), triethylamine (0.2 ml, 0.0014 mol), tetrabutylphosphonium bromide (0.15 g, 0.00044 mol) and dry toluene (40 ml). The reaction mixture was allowed to proceed at reflux (approximately 145 C.) for 18 hours. The reaction mixture was sampled and tested by HPLC which indicated a yield of 4,4′-bis(N-methylphthalimide)sulfide of 10% (0.04 g).

Statistics shows that 2-Methyl-5-nitroisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 41663-84-7.

Reference:
Patent; General Electric Company; US4625037; (1986); A;,
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Related Products of 667463-64-1, 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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

The synthetic route of 6-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H15NO3

General procedure: A round-bottom flask was charged with the corresponding alcohol (1.0 equiv) followed by the addition of Et2O (0.1 M). The solution was cooled to 0 C. Next, oxalyl chloride (2.0 equiv) was added dropwise. The homogeneous reaction mixture was allowed to warm to ambient temperatureand stir for 1-18 h. The reaction was cooled to 0 C and quenched by slow addition of H2O (100.0 equiv). After stirring for 1 h at room temperature, the resulting mixture was transferred to a separatory funnel, and the aqueous layer mixture was extracted with three portions of Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure affording the desired oxalic acid. All the oxalates were used without further purification.

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:
Article; Gonzalez-Esguevillas, Maria; Miro, Javier; Jeffrey, Jenna L.; MacMillan, David W.C.; Tetrahedron; vol. 75; 32; (2019); p. 4222 – 4227;,
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Application of 1055412-47-9, 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. 1055412-47-9, name is su-5614 belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (120 mg, 0.44 mmol), morpholine (39 muL, 0.44 mmol) and paraformaldehyde (20 mg, 0.66 mmol) in 8 mL of dioxane and 2 mL of EtOH was heated to 80 C. for 15 h. The reaction mixture was cooled to room temperature and treated with morpholine (25 muL, 0.28 mmol) and paraformaldehyde (16 mg, 0.50 mmol) The reaction mixture was heated at 80 C. for 4 h. The reaction mixture was cooled to room temperature and partially concentrated under a nitrogen stream. The reaction mixture was cooled to -20 C. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (85 mg, 52%) as an orange solid.

The synthetic route of su-5614 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2004/102509; (2004); 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. Product Details of 6941-75-9

Preparation of 5-bromo-2,3-dihydro-1H-isoindole (13); 564.2 ml of a 1M borane/THF solution are added dropwise to 42.5 g (188 mmol) of 5-bromoisoindole-1,3-dione in 300 ml of THF (dry) at -5 C. over a period of 60 min. The mixture is subsequently stirred for 2 h at 22 C. and then for 16 h at 80 C. The mixture is then cooled to 0 C., before 200 ml of methanol (exothermic.) and 200 ml of 2M hydrochloric acid are slowly added. The resultant mixture is stirred for 3 h at 80 C., cooled to 22 C., and 100 ml of water are added. The aqueous solution is extracted three times with 150 ml of dichloromethane each time, dried over sodium sulfate, filtered and evaporated to dryness: 5-bromo-2,3-dihydro-1H-isoindole; yield 15.4 g of ?13? (41.3%); MW 198.06; Rt 1.099 min (?polar? method).

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

Reference:
Patent; Merck Patent Gesellschaft Mit Beschrankter Haftung; US2010/311745; (2010); A1;,
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Electric Literature of 87-48-9, 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. 87-48-9, name is 5-Bromoindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 90a: 5-Bromoindolin-2-one (Compound 0601-194)To a mixture of 5-bromoindole-2,3-dione (2.25 g, 10 mmol), ethyleneglycol (45 mL) and hydrazine hydrate (1.06 g, 21.10 mmol) was added KOH (1.68 g, 30 mmol). The reaction mixture was stirred at 80C for 4 hours. The mixture was cooled to room temperature and poured into ice cold water and the mixture was adjusted to pH 1-2 with 12N hydrochloric acid and stirred at room temperature for 12 hours. The mixture was filtered and solid was washed with water (5 mL) and dried to get the crude product which was purified by column chromatography on silica gel (methanol in dichloromethane, 0.5% v/v) to give 0601-194 (785 mg, 37%) as a yellow solid. LCMS: 214 [M+l]+. 1H-NMR (400 MHz. OMSO-de) delta 3.51 (s, 2H), 6.76 (d, J= 8.0 Hz, 1H), 7.34 (dd, J= 8.0, 2.0 Hz, 1H), 7.38 (m, 1H), 10.49 (s, 1H).

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-Bromoindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng; WO2011/130628; (2011); A1;,
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Synthetic Route of 954-81-4, 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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 3-1 (5.0 g, 17 mmol) was dissolved in dimethylformamide (DMF, 30 mL), and sodium azide (1.4 g, 1.3 eq.) was added. The reaction mixture was allowed to stir overnight, whereupon it was concentrated in vacuo to yield a white residue. The residue was dissolved in DCM, filtered through a silica gel plug, and solvent removed to afford N-[5- (azido)butyl]phthalimide (4.0 g, 91%) as a colorless thick oil. ?HNMR(300IVIHz, CDC13): = 1.30-1.44 (m, 2H), 1.50-1.75 (m, 4H), 3.21 (t, J= 7.5 Hz, 2H), 3.63 (t, J = 7.5 Hz, 2H), 7.60-7.70 (m, 2H), 7.75-7.80 (m, 2H). ?3C NIVIR(75 IVIFIz CDC13): = 23.8, 27.9, 28.2, 37.4, 51.0, 123.0, 131.9, 133.7, 168.2.

The chemical industry reduces the impact on the environment during synthesis N-(5-Bromopentyl)phthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LUMIPHORE, INC.; BUTLIN, Nathaniel G.; MAGDA, Darren; XU, Jide; (114 pag.)WO2016/106241; (2016); A1;,
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Application of 1336963-95-1, These common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-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.

2-Amino-4-bromo-3-fluorobenzoic acid To a solution of 6-bromo-7-fluoroindoline-2,3-dione (1.41 g, 5.80 mmol) in 2 N NaOH (15 mL), H2O2 solution (30%, 3 mL) was added at 0 oC and the resulting mixture was stirred at 0 oC for 30 min. After stirring at room temperature for 16 h, the mixture was poured into ice-water, and the solution was acidified with conc. HCl solution. The precipitate was collected by filtration and dried in the air to afford the desired product (1.2 g, 89% yield) as a white solid.

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; WU, Tao; REN, Pingda; LIU, Yi; LIU, Yuan; LONG, Yun, Oliver; WO2015/54572; (2015); A1;,
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