Author: Jessica.F

Synthetic Route of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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: Procedure C: A solution of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (1, 0.4 g, 3.0 mmol), 5-bromo-2-(4-methoxybenzyl) isoindolin-1-one (2, 1.0 g, 4.5 mmol) and potassium phosphate (1.91 g, 9.0 mmol) in 1, 4-dioxane (15 ml) was degassed with nitrogen for 10 min. Copper (I) iodide (0.28 g, 1.5 mmol) and trans-1, 2-diaminocyclohexane (0.17 g, 1.5 mmol) were added and the reaction was refluxed at 90 C. for 16 h. Progress of the reaction was monitored by TLC. After completion, solvent was removed under reduced pressure. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 2-(4-methoxybenzyl)-5-(4-methyl-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.55 g, 47%;

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-(4-bromobutyl)isoindoline-l,3-dione (3.33 g, 11.8 mmol), tert- butyl piperazine-l-carboxylate (2.2 g, 11.8 mmol) and Et3N (4.9 ml, 35.4 mmol) in CH3CN (50 mL) is heated at reflux for 16 h. The mixture is cooled and the solvent is evaporated. The residue is partitioned between EtOAc (70 mL) and water (70 mL). The organic layer is washed with brine (40 mL), dried (Na2S04) and evaporated. The residue is purified by flash column with 1:1 Hexane/EtOAc gives colorless oil (3.91 g, 85%).’HNMR (CDCI3,) delta: 7.83 (dd, 2H), 7,71 (dd, 2H), 3.71 (t, 2H), 3.41 (t, 4H), 2.34- 2.38 (m, 6H), 1.67-1.70 (m, 2H), 1.50-1.56 (m, 2H), 1.45 (s, 9H).LC-MS M+1: 388.12;

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

Reference:
Patent; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; HAN, Bingsong; KUNTZ, Judith D.; LIN, Jian; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; WO2012/154194; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

A mixture 6-chloroindolin-2-one (100 mg, 0.60 mmol), 3-(3,3,4,4- tetramethylborolan-l-yl)pyridine (184 mg, 0.90 mmol), Pd2dba3 (5.4 mg, 0.0060 mmol) and powdered K3PO4 (252 mg, 1.2 mmol) in w-BuOH (2 mL) was degassed by evacuation and refilling with Ar. Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2- yl)phosphine (11.4 mg, 0.024 mmol) was added under the atmosphere of Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 100 0C for 99 min. Later the reaction was cooled to rt and treated with degassed H2O (0.25 mL). The mixture was reheated under microwave irradiation at 110 0C for 1 h. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (0 to 6 %) in DCM as the eluent to provide the title compound as a pale yellow solid (100 mg, 80 %). %). 1H NMR (400 MHz, CD3OD) delta ppm 8.77 (d, J=I.52 Hz, 1 H), 8.52 (dd, J=4.80, 1.52 Hz, 1 H), 8.05 – 8.10 (m, 1 H), 7.52 (dd, J=7.33, 4.80 Hz, 1 H), 7.39 (d, J= 7.6 Hz, 1 H), 7.30 (dd, J=7.71, 1.39 Hz, 1 H), 7.17 (s,l H), 3.59 (s, 2 H); MS ESI 211.0 (100) [M + H]+, calcd for [C13H10N2O + H]+ 211.2.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6941-75-9, 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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromoisoindoline- 1, 3-dione (3) (25 g, 110.6 mmol, 1.0 equiv) in THF (60 mL) was added BF3 (30 g, 442.4 mmol, 4.0 equiv) dropwise at 0 C. The mixture was stirred at 0 C for 1.5 h and BH3 (650 ml, 1.0 M, 6.0 equiv) was added dropwise at 0 C. Then the mixture was heated to 80C for 20 h and quenched by addition of methanol (100 mL) dropwise for 1 h at 0C. The mixture was concentrated to give a crude product of 5-bromoisoindoline (4) (22 g), which was used for next step directly.

The chemical industry reduces the impact on the environment during synthesis 5-Bromoisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; QI, Xiangbing; LOU, Mingliang; WU, Enlong; CHEN, Peihao; WU, Qingcui; (41 pag.)WO2018/95260; (2018); 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 1127-59-9 as follows. Recommanded Product: 1127-59-9

General procedure: A solution of isatin derivatives 1 (0.4 mmol), 3-methyl-4-nitro-5-alkenyl-isoxazoles 2 (0.6 mmol) and proline or thioproline or sarcosine (0.8 mmol) in 10.0 mL of CH3CN at 80 °C for 24 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc5:1-3:1) to furnish the corresponding products 3-5.

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Xiong-Wei; Yao, Zhen; Yang, Jun; Chen, Zhi-Yong; Liu, Xiong-Li; Zhao, Zhi; Lu, Yi; Zhou, Ying; Cao, Yu; Tetrahedron; vol. 72; 10; (2016); p. 1364 – 1374;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 13861-75-1, These common heterocyclic compound, 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, 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.

[0272] To a cooled (0C) solution of spiro[cyclopropane-l,3′-indolin]-2′-one (prepared according to methods described in J. Med. Chem. 1987, 824-829; J. Med. Chem. 1992, 163-172; U.S. Patent 5,182,397) (1.0 g, 6.21 mmol) in NN-dimethylformamide (5 mL), was added sodium hydride (0.149 g, 6.21 mmol), followed by addition of l-bromo-3-chloropropane (0.733 mL, 7.45 mmol, d = 1.6). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgS04, filtered and isolated by Biotage flash chromatography (10-40% ethyl acetate/hexanes) to obtain the title compound (1.1 g, 68%); ¾ NMR (DMSO-i 6): delta 1.50-1.54 (m, 2H), 1.56-1.61 (m, 2H), 2.01- 2.15 (m, 2H), 3.67 (t, 2H, J= 6.4 Hz), 3.86 (t, 2H, J= 6.8 Hz), 6.97-7.03 (m, 2H), 7.11 (d, 1H, J= 8 Hz), 7.22-7.27 (m, 1H); MS for Ci3H14ClNOm/z 236.04 (M+H)+.

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, molecular formula is C22H19N3O6, 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. Computed Properties of C22H19N3O6

This example relates to preparation of the compound (5S)-4-{4-[5- (aminomethyl)-2-oxo-1 ,3-oxazolidine-3-yl]phenyl}morpholine-3-one nitrate, step c) of the process. 17.0 kg of the compound (IV) obtained in example 2, 170 kg of ethanol and 20.4 kg of methylamine in aqueous solution at 40% by weight, are loaded into a reactor. The temperature of the reactant system is then brought to about 60 C and maintained at this value for 3 hours. At the end of the reaction, the mass obtained is distilled under vacuum until a dense residue is obtained; 170 kg of ethanol and 34.0 kg of water are added to the residue. 4.47 kg of an aqueous solution at 65% by weight of nitric acid, are slowly added to the mixture thus obtained, maintained at a temperature of about 30 C. At the end of the addition of the acid, the precipitate is filtered and washed with 25.5 kg of ethanol and lastly oven-dried. 1 1 .0 kg of the desired compound (V) are obtained, with a reaction yield equal to 76.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 446292-08-6, its application will become more common.

Reference:
Patent; ERREGIERRE S.P.A.; FERRARI, Massimo; GHEZZI, Emanuele; GHEZZI, Marcello; WO2015/198259; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1.A solution of 9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydrofuro[3,4- d][l,3]dioxol-4-yl)-9H-purin-6-amine (400 mg, 1.3 mmol) and 3-(l,3-dioxoisoindolin-2- yl)propanal (293 mg, crude 1.44mmol) in DCE (8 mL) were stirred at rt for 0.5 h, then NaBH(OAc)3 (416 mg, 1.96 mmol) was added. The reaction was stirred at rt overnight. The reaction was quenched with aqu. sat. NaHC03 (2 mL), extracted with DCM (10 mLx3), washed with brine (10 mL), dried and concentrated. The residue was purified by prep-TLC (DCM : MeOH = 10 : 1) to the title compound (350 mg, Yield 43%). NMR (500 MHz, MeOD): delta 8.28 (s, 1H), 8.21 (s, 1H), 7.83-7.76 (m, 4H), 6.14(d, J = 3.5 Hz, 1H), 5.46-5.44 (m, 1H ), 5.01-4.99 (m, 1H), 4.32 (br s, 1H), 3.65-3.62 (m, 2H), 2.85-2.83 (m, 2H), 2.57-2.53 (m, 2H), 1.79-1.76 (m, 2H), 1.58 (s, 3H), 1.37 (s, 3H) ppm; ESI-MS (m/z): 494.2[M+1]+.

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, 3-(1,3-Dioxoisoindolin-2-yl)propanal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,3-dihydro-1 H-isoindole (0.3 mL) in dichloromethane (5 mL)Triethylamine (0.7 mL)And the mixture was ice-cooled to 0 C.,2-Bromoacetyl bromide (0.4 mL) was added dropwise, followed by stirring at room temperature for 18 hours.Water was added to the reaction solution, the mixture was extracted with dichloromethane and washed with saturated brine.The organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure to obtain a residue.Purification by silica gel column chromatography (hexane-ethyl acetate)2-Bromo-1- (2,3-dihydro-1 H-isoindol-2-yl)Ethan-1-one281 mg (yield 47%) was obtained.

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

Reference:
Patent; NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY; YANAGISAWA, KATSUHIKO; KAWAI, AKIYOSHI; (139 pag.)JP2017/171619; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 897957-06-1

To I-5.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R11 (54.4 g, 241 mmol) and potassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C. for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgSO4 and concentrated. The residue is purified via flash chromatography (cyclohexane/EA=70:30). Yield 72%, m/z 274 [M+H]+, rt 0.67 min, LC-MS Method V011_S01.

According to the analysis of related databases, 897957-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275159; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem