Author: Jessica.F

Application of 102359-00-2,Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

An oven-dried round-bottom flask was charged with 2-oxoindoline-5- carboxylic acid (89 mg, 0.500 mmol), TBTU (193 mg, 0.600 mmol), HOBt hydrate (81 mg, 0.600 mmol), DIPEA (0.13 mL, 0.750 mmol) and DMF (3.0 mL) and stirred for 5 minutes. Methyl amine (0.75 mL of a 2.0 M solution in THF) was then added and reaction was stirred for 4 hours at which time NaHCO3(Sat ) (2mL) was added. Solvents were removed in vacuo and the residue was purified by column chromatography (silica gel, 92:8 CH2Cl2ZMeOH) to give the title compound (11 mg, 12 %). IH NMR (400 MHz, CD3OD) delta ppm 7.69 – 7.75 (m, 2 H), 6.94 (d, J=8.1 Hz, 1 H), 3.58 (s, 2 H), 2.97 (s, 3 H); MS ESI 191.0 [M + H]+, calcd for [C10H10N2O2 + H]+ 191.08.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxoindoline-5-carboxylic Acid, its application will become more common.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
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Application of 3485-84-5,Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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.

Preparation 1 2-{2-[4-(2-Hvdroxy-ethvD-phenyl1-vinyl)-isoindole-1 ,3-dione; To a solution of 2-(4-bromophenyl)ethanol (48.3g) in acetonitrile (480 ml) were added diisopropylethylamine (46.6g), N-vinylphthalimide (43.7g) and tri-o-tolylphosphine (7.31g) and the mixture was purged with nitrogen gas three times. Palladium acetate (2.7g) was added and the mixture was stirred at 9O0C for 21 hours under nitrogen. The reaction was cooled and the precipitated product collected by filtration. The resulting solid was re-dissolved in dichloromethane and ethyl acetate and filtered through silica gel. The filtrate was concentrated in vacuo to give the title compound, 24g. 1H NMR (400MHz, CDCI3) delta = 2.81 -2.84 (t, 2H), 3.82-3.90 (t, 2H), 7.23-7.26 (d, 2H), 7.32-7.36 (d, 1 H), 7.40-7.43 (d, 2H), 7.61-7.64 (d, 1 H), 7.66-7.78 (d, 2H), 7.86-7.88 (d, 2H) ppm.

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

Reference:
Patent; PFIZER LIMITED; GLOSSOP, Paul Alan; LANE, Charlotte Alice Louise; WO2010/7561; (2010); A1;,
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Electric Literature of 169037-23-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
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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. SDS of cas: 675109-26-9

O2O3] &bromoisoindolin4-orse (1050 mg, SM m.mol% copper powder (32 mg, 0.5 mmol) and methylamine (40% in F120, 2.7 mL) were placed in a pressure vess& and the sealed reaction was heated at 105 C overnight. The reaction mixture was poured into ethyl acetate (150 niL) and washed with saturated NH4CI solution. The organic layer was dried over sodium sulfate, filtered and concenflted. The volatile was removed in vacua and the residue was then purified by silica gel chromatography eluting with MeOH and dichloromethane Rf 0.2, 5% MeOH in DCIVO to afford 300mg of the title compound. MS (m/z): 163.13 [M+H]t HPLC retention time 0.17 mm (248% acetonitrile: water with 0.05% trifluoroacetie acid). ?H NMR (400 MHz, dmso) 8 8.28 (s 1K), 7.20 (d, J= 8.2 Hz, 1H), 6.75 (dd, J 8.2, 2.2 Hz5 lH), 6.68 (d, J= 2.1 Hz, 1K), 5.83 (d, J 5.0 Hz, IH), 4.15 (s, 2K), 2.66 (d, J= 5,1 Hz, 3Ff).

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; GILEAD SCIENCES, INC.; BONDY, Steven, S.; CHOU, Chien-Hung; LINK, John, O.; TSE, Winston, C.; WO2015/130964; (2015); A1;,
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Electric Literature of 3335-98-6, 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. 3335-98-6, name is 1-Phenyloxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 (3×30 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.

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

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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Reference 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.

Step C: (Z)-5-Bromoisoindolin-1-one O-benzyl oxime: 5-Bromoisoindolin-1-one (3.00 g, 14.1 mmol) was suspended in 100 mL chloroform at 0 C. Triethyloxonium tetrafluoroborate (4.03 g, 21.2 mmol) was added in a single portion to the mixture and the suspension was stirred from 0 C. to ambient temperature over the 48 hours. The reaction was concentrated and the residue dissolved in 150 mL ethanol and cooled to 0 C. O-benyzyl hydroxylamine HCl (4.52 g, 28.3 mmol) and sodium carbonate (4.50 g, 42.4 mmol) were added, and the reaction was stirred from 0 C. to ambient temperature for 18 hours, then concentrated, diluted with ethyl acetate, washed with 10% citric acid, dried over sodium sulfate, filtered and concentrated to a solid. The solid was purified by silica gel chromatography with 100% dichloromethane (1.69 g, 37%).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
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Electric Literature of 101207-45-8, 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. 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-(4-methylbenzyl)isoindoline-l,3-dione (1 g, 3.8 mmol) and hydrazine hydrate (752 mg, 15 mmol, 730 pL) in MeOH (10 mL) was stirred at 20C for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (0928) (dichloromethane:methanol (with 5% ammonia in water) = 0:1 to 5:1) to give p-tolylmethanamine (160 mg).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Methylbenzyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (275 pag.)WO2019/115566; (2019); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 181140-34-1 as follows. Recommanded Product: 181140-34-1

A mixture of 2,3-dihydro-1 /-/-inden-2-amine (5.0 g, 24.61 mmol) and (R)-2-(oxiran-2- ylmethyl)isoindoline-1 ,3-dione (4.91 g, 36.91 mmol) in EtOH (100 mL) was heated at reflux overnight. After cooling to room temperature, triethylamine (9.94 g, 98.44 mmol) and (0472) (Boc)20 (10.74 g, 49.22 mmol) were added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated and purified by column (EtOAc / petroleum ether = 1/4, v/v) to give the title compound (5.4 g, 50%) as an oil.

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul Anthony; (88 pag.)WO2017/153519; (2017); A1;,
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Electric Literature of 239463-85-5, A common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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.

In a 500 ml reaction vessel150 g of purified water and 135 g of ethyl acetate were added and 40.4 g of potassium carbonate was dissolved.To this was added 15 g of 5-[(2R)-2-aminopropyl]-1-[3-(benzyloxy)propyl]2,3-dihydro-1H-indole-7-carbonitrile was added,And stirred for 2 hours.The ethyl acetate layer was separated, dehydrated with anhydrous sodium sulfate and concentrated, and then 50 g of toluene,12 g of 2-[2-(2,2,2-trifluoroethoxy)phenoxy] ethanol-1-methanesulfonate,3.3 g of sodium carbonate was added, and the mixture was stirred under reflux.After completion of the reaction, an aqueous solution of sodium hydrogencarbonate and ethyl acetate were added, layered and then dehydrated with anhydrous sodium sulfateAnd concentrated under reduced pressure to give 2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile (Purity: 79.9%, dialkyl content: 12.0%).

The synthetic route of 239463-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanseo Chem Co., Ltd.; Oh Min-geun; Kim Gi-nam; Seo Gi-hyeong; Park Seong-tae; Cho Dong-ho; (17 pag.)KR2016/109736; (2016); A;,
Indoline – Wikipedia,
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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. 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. name: 5-Bromoindolin-2-one

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
Indoline – Wikipedia,
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