Category: indolines-derivatives

Electric Literature 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.

2-Oxoindoline-5-carboxylic acid (0.214 g, 1.21 mmol), O-(BENZOTRIAZOL-L-YL)-N, N, N, N- TETRAMETHYLURONIUM TETRAFLUOROBORATE (0. 462 G, 1.44 mmol), 1-HYDROXYBENZOTRIAZOLE hydrate (0.194 g, 1.44 mmol) and N, N-diisopropylethylamine (0.3 ML, 1.71 mmol) were suspended in a mixture of acetonitrile (4 mL) and N, N-DIMETHYLFORMAMIDE (1 ML) and stirred at room temperature for 30 min. Benzylamine (0. 155 g, 1.45 mmol) was added and stirring was continued for 12 h. The solvent was removed in vacuo and the residue was separated between chloroform and a saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with chloroform (3X30 mL). The combined organic layers were dried over sodium sulfate. Filtration and removal of the solvent in vacuo yielded the crude product which was purified on a silica gel column using a gradient chloroform/methanol, (100: 1 to 1: 1), as the eluent to give 0.104 g (30% yield) of the title compound as a solid : 1H NMR (DMSO-D6, 400 MHz) 8 10. 60 (s, 1 H), 8.85 (m, 1 H), 7.77 (m, 2 H), 7.29 (m, 4 H), 7.21 (m, 1 H), 6.85 (d, J = 11 HZ, 1 H), 4.45 (d, J = 6 Hz, 2 H), 3.52 (s, 2 H); MS (ES) TIZZY 267 (M++1).

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; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
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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. 893620-44-5, name is 6-Bromo-5-fluoroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 6-Bromo-5-fluoroindolin-2-one

a) 6-Bromo-5-fluoro-3,3-dimethylindolin-2-one To a solution of potassium tert-butoxide (9.27 g, 82.6 mmol) in dry THF (50 ml) under icebath cooling was added 6-bromo-5-fluoroindolin-2-one (example 20c, 3.8 g, 16.5 mmol) in portions, followed by copper (I) bromide-dimethyl sulfide complex (340 mg, 1.65 mmol). After cooling to 2C methyl iodide (4.92 g, 2.17 ml, 34.7 mmol) was added slowly over a period of 30 minutes. The reaction mixture was warmed to room temperature, stirred for 16 hours, then cooled to 0C and carefully quenched with saturated ammonium chloride solution. The mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent and followed by trituration with diethyl ether. The title compound was obtained as yellow solid (3.6 g). MS ESI (m/z): 258.0/ 260.0 [(M+H)+]. 1H NMR (CDCI3, 400 MHz): (ppm) = 10.44 (bs, 1H), 7.48-7.45 (m, 1H), 7.05-7.04 (m, 1H), 1.25 (s, 6H).

According to the analysis of related databases, 893620-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
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Reference of 552330-86-6, The chemical industry reduces the impact on the environment during synthesis 552330-86-6, name is 5-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

Combine 4-bromo-2-bromomethyl-benzoic acid methyl ester (3.0 g, 9.7 mmol) and 7M NH3 in methanol (100 mL, 700 mmol) in a sealed tube and heat in a 40C oil bath for 18 hours. Cool the resulting suspension to room temperature and filter to obtain 1.5 g of 5-bromo-2, 3-dihydro-isoindol-1-one (72 %). Combine 5-bromo-2, 3-dihydro-isoindol-1-one (1. 1 g, 5.0 mmol), bis- pinocalatodiboron (1.4 g, 5.5 mmol), [1, l’-Bis (diphenylphosphino) – ferocene] dichloropaladium (II) complex with dichloromethane (408 mg, 0.5 mmol) and potassium acetate (1.5 g, 15.0 mmol) in a 200 mL flask with a septum. Add dimethyl sulfoxide (27 mL) and heat in a 90C oil bath for 18 hours. Cool the resulting slurry to room temperature and dilute with water (100 mL). Extract the resulting slurry with dichloromethane (3 x 75 mL). Wash the combined organic layers with brine (40 mL), dry (Na2S04), filter and concentrate in vacuo to obtain 1.6 g of a mixture of the title product and bis-pinocalatodiboron (1: 0.05), which is used without further purification.

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; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
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Synthetic Route of 3485-84-5, 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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows.

A mixture consisting of N-vinylphthalimide (2.0 g, 11.5 mmol), vinyltrimethylsilane (2.03 mL, 13.8 mmol), RuHCl(CO)(PCy3)2 (0.167 g, 0.23 mmol), and 23 mL of dry toluene was placed under an argon atmosphere in a 150 mL Schlenk bomb flask fitted with a plug valve and heated at 100 C for 24 h to complete the reaction (GC analysis). Next, after cooling the reaction mixture to room temperature, 92 mL of acetonitrile and N-iodosuccinimide (5.18 g, 23.0 mmol) were added and the mixture was stirred for 24 h at room temperature. After this time the solvents were evaporated and the reaction mixture was quenched with aqueous Na2S2O3, extracted with hexane, and concentrated to dryness. The final product was purified by column chromatography on silica gel, eluting with n-hexane/EtOAc (50/2).

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

Reference:
Article; Pawlu?, Piotr; Franczyk, Adrian; Walkowiak, J?drzej; Hreczycho, Grzegorz; Kubicki, MacIej; Marciniec, Bogdan; Tetrahedron; vol. 68; 18; (2012); p. 3545 – 3551;,
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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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C14H13NO3

(A) 15gm (0.061 Tmole) 4-phthalimido cyclohexanone was dissolve in 150ml methanol.Heat the mass to 40C. Add Br2 solution (9.8gm Br2 in 25ml of methanol) and 0.25gm ofAids under stirring. Stop stirring and allow initiating bromination and finding clearsolution then add remaining quantity of Br2 solution and stir for 10-15mins. Add 10mlwater and stir for lOmins more. Then filter the white solids obtain .Dry it at 50C for 2-3hrs.YIELD: 12.5gm(62.8%)

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; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
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Synthetic Route of 2058-72-2, 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 2058-72-2 as follows.

General procedure: To a solution of ligand 1(11mol %) in ethanol (2 ml) was added coppersalt (10 % mol), After 5 hours the color of the solution changed from blue-green to purple. Then,dipolarophile (0.20 mmol) has been added andstirred about 30 min. Next, a mixture of isatin derivatives (0.20 mmol) and (S)-proline (0.21 mmol), in 3 ml ethanol/dichloromethane (5/1) was added to reaction mixture.After completion of the reaction (monitored by TLC), reaction was diluted withdiethyl ether and filtered through a pad of silica gel. The organic layer wasconcentrated in vacuum to furnish the products, which were recrystallized fromethanol.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Salahi, Farbod; Taghizadeh, Mohammad Javad; Arvinnezhad, Hamid; Moemeni, Mehdi; Jadidi, Khosrow; Notash, Behrouz; Tetrahedron Letters; vol. 55; 9; (2014); p. 1515 – 1518;,
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Adding a certain compound to certain chemical reactions, such as: 20870-79-5, name is 5-Nitroindolin-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 20870-79-5, Computed Properties of C8H6N2O3

5-Amino-2-Oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

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-Nitroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen. Inc.; US2003/100555; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, 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 88150-75-8, Formula: C16H17NO6

To a solution of ethyl 4-(2-phthalimidoethoxy)acetoacetate in toluene was added 3000 ml of isopropyl alcohol, 564 g of 2-chlorobenzaldehyde was added with stirring, 17 5g acetic acid, 24.8g piperidine; 20 ~ 30 C, stirring 9 ~ 10h, adding 589g beta-aminocrotonic acid methyl ester, heating to 55 ~ 58 C, and stirring at 55 ~ 58 C reaction, stirring 7h sampling, TLC plate to confirm the end of the reaction, cooling to below 25 C, adding 3200ml acetic acid; then seeded to 0 ~ 5 C, the same temperature for 5h, crystallization; filtration crystallization, with 800ml isopropyl alcohol washing, the wash was run twice (400 ml each) and dried under reduced pressure to give 1611 g of phthaloyl amlodipine in a yield of 76.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; Qianhui Pharmaceutical (Anhui) Co., Ltd.; Yang Huilai; Mao Jie; Sun Xuexi; (7 pag.)CN106749187; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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, 2-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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Related Products of 17564-64-6, 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. 17564-64-6 name is 2-(Chloromethyl)isoindoline-1,3-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.

Example 17: (E)-3-[3′-Adamantan-l-yl-4′-(l,3-dioxo-l,3-dihydroisoindol-2- ylmethoxy)-biphenyl-4-yl] -acrylic acid ST5632AA1; STEP 1: A solution of (E)-3-(3′-adamantan-l-yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-hutyl ester (200 mg, 0.464 mmol), N-chloromethylphthalimide (91 mg, 0.464 mmol), K2CO3 (70 mg, 0.464 mmol) and NaI (70 mg, 0.464 mmol) was stirred overnight at RT in the dark. The solvent was evaporated and the residue was taken up in EtOAc. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. 3-[3′- Adamantan-l-yl-4′-(l,3-dioxo-l,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4- yl] acrylic acid tert-hutyl ester was obtained after purification on silica gel (EtOAc/hexane 15:85) in 55%yield (150 mg).1H NMR (DMSO-ds) delta: 7.30-8.05 (m, 12H); 6.55 (d, J = 16 Hz, IH); 5.70 (s, 2H); 2.05 (s, 6H); 1.95 (s, 3H); 1.60 (s, 6H); 1.50 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; CABRI, Walter; GIANNINI, Giuseppe; BATTISTUZZI, Gianfranco; ALLOATTI, Domenico; PISANO, Claudio; DALLAVALLE, Sabrina; BRUNETTI, Tiziana; WO2010/72727; (2010); A1;,
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