Category: 552330-86-6

Electric Literature 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 B: 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l-one [0231] 5-Bromoisoindolin-l-one (0.066 g, 0.311 mmol), bis(pinacolato)diboron (0.119 g, 0.467 mmol), potassium acetate (0.092 g, 0.934 mmol), and PdCl2(dppf)CH2Cl2 adduct (0.013 g, 0.016 mmol) were suspended in DMA (0.6 mL), degassed with N2, and stirred in a sand bath at 100C overnight. The reaction mixture was subsequently cooled, diluted with EtOAc (10 mL), and passed through a syringe filter. The filtrate was diluted with water (10 mL) and the layers were separated. The aqueous layer was washed with EtOAc (2 x 5 mL). The organic layers were combined and concentrated in vacuo to give the title compound as brown oil, which was 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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LAWSON, John David; SABAT, Mark; SMITH, Christopher; WANG, Haixia; CHEN, Young K.; KANOUNI, Toufike; WO2013/148603; (2013); 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 552330-86-6 as follows. COA of Formula: C8H6BrNO

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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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. 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. Product Details of 552330-86-6

Step A: 5-Bromo-1-oxo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester To a solution of 5-bromo-2,3-dihydro-isoindol-1-one (10.0 g, 47.4 mmol) in THF (100 mL) was added a solution of (Boc)2O (20.6 g, 94.5 mmol), and DMAP (0.57 g, 4.6 mmol). The reaction mixture was stirred at ambient temp overnight. Upon completion, the reaction mixture was concentrated in vacuo, and the residue was purified by flash column chromatography (EA:PE=1:10) to afford the title compound (13 g, 88%).

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

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; Chen, Young K.; Wallace, Michael Brennan; (110 pag.)US2017/183325; (2017); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 552330-86-6

To a 25 mL rmmd-boitom t1ask was added 5-bromo-2,3-dihydro-H-1-isoindol-1-one10 135a (500 mg, 2.36 mmol, 1.0 equiv.), di-tert-butyl dicarbonate (800 mg, 3.67 mmol, 1.5equiv.), 4-dimethylaminopyridine (30 mg, 0.25 mmol, 0.1 equiv.), and tetrahydrofuran (5mL). The resulting mixture v.¡¤as stirred at room temperatme overnight. The mixture wa.-.:diluted with 500 mL of brine and extracted with ethyl acetate (250 mL x 3). The organicextracts Vere combined, dried over anhydrous sodium sulfate, and concentrated under15 vacuum. The residue was pmified by Fla.-.:h-Prep-HPLC using the following conditions(IntelFlash-l): Column, silica gel: mobile phase: EA: PE”‘O: 100 increasing toEA: PE”’20:80within 25 min; Detector, UV 2.54 nm. Removal of solvents gave tert-butyl 5-bromo-1-oxo-2,3-dihydro-lH-isoindole-2-carboxylate l35b ( 6.59 mg, 90%) as a light yellow solid.

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; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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Reference 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.

A mixture of 5-bromoisoindolin-1-one 1 (5 g, 23.6 mmol), THF (50 mL), 4-dimethylaminopyridine (288 mg, 2.36 mmol) and di-tertbutyl dicarbonate (8 g, 35.4 mmol) was stirred for overnight at room temperature. The resulting mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed with 10% citric acid. The organic layer was dried over Na2504, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate/heptane (1:1) to afford the compound 2 (7.1 g, 96%) as a white solid. LC/MS (ESI+): mlz 313.2 (M+H).

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
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Synthetic Route of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-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.

Intermediate No.165 *romo-2 -trimethyl-2 -dihvdro-l/y soindol-l-one5-Bromo-2,3-dihydro-lH-isoindol-l-one (150 mg, 0.71 mmol) was dissolved in DMF (3.5 mL) and stirred at ambient temperature. NaH (85 mg, 2.1 mmol, 60% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir for 15 minutes before Mel (151 mg, 1.06 mmol) was added. The mixture was allowed to stir at ambient temperature for 30 minutes before water (10 mL) was carefully added. The mixture was extracted with EtOAc, and the organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-20% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound.LRMS (ESI) calc’d for Ci iH12BrNO [M+H]+: 254, Found: 254.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromoisoindolin-1-one

Step 1: 5-(Benzylthio)isoindolin-1-one (0478) (0479) Benzyl mercaptan (11.71 g, 94.32 mmol) was added to 5-bromoisoindolin-1-one (10 g, 47.16 mmol) and sodium 2-methyl-2-butoxide (5.19 g, 47.16 mmol) in DMF (100 mL) under nitrogen. The resulting mixture was stirred at 100 C. for 2 hours. The reaction mixture was quenched with water (300 mL) and extracted with EtOAc (3¡Á300 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to afford 5-(benzylthio)isoindolin-1-one (7.00 g, 58.1%) as a yellow solid. (0480) LC/MS: m/z=256 [M+H]+. 1H NMR (300 MHz, DMSO-d6) delta 4.33 (s, 2H), 4.35 (s, 2H), 7.23-7.61 (m, 8H), 8.48 (s, 1H).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Electric Literature 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.

To a solution of 5-bromo-2,3-dihydro-isoindol-1-one (200.00 mg; 0.90 mmol; 1.00 eqf.) in anhydrous 1 ,4-dioxane (4.00 mL), bis(pinacolato)diboron (255.40 mg; 0.99 mmol; 1.10 eqf.), KOAc (307.79 mg; 3.14 mmol; 3.50 eqf.) and dppf (49.68 mg; 0.09 mmol; 0.10 eqr.) are added. RM is purged with argon and Pd(dppf)CI2 (65.54 mg; 0.09 mmol; 0.10 eqf.) is added. RM is stirred at 1 10C for 16 h. RM is filtered through a pad of Celite and partitioned between EtOAc and water. The aqueous phase is washed with EtOAc, combined organic layers are washed with brine, dried over Na2S04 and concentrated in vacuo to afford 5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-2,3-dihydro- isoindol-1-one (377.00 mg; 68 %; 42 % by UPLC) as a brown powder. Crude product is used for futher reactions.

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

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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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. Application In Synthesis of 5-Bromoisoindolin-1-one

[0264] 5-Bromo-2,3-dihydro-isoindol-l-one (l.OOg, 4.72mmol), l-bromomethyl-4-methyl-benzene (1.14g, 6.14mmol) and cesium carbonate (3.08g, 9.44mmol) were suspended in anhydrous NMP (lOmL). The mixture was immersed in a 60C oil bath for 16.5 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Column chromatography (20% to 40% ethyl acetate/hexanes) provided the title compound as a yellow solid (1.18g, 79%). 1H NMR CDC13: 7.76 (d, 1H), 7.62 (d, 1H), 7.55 (s, 1H), 4.76 (s, 2H), 4.24 (s, 2H), 2.35 (s, 3H).

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

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 552330-86-6, name is 5-Bromoisoindolin-1-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 552330-86-6, Quality Control of 5-Bromoisoindolin-1-one

Step 3 5-(4,4,5 ,5-Tetramethyl-[ 1 ,3 ,2]diotaoxaborolan 2-yl) 2,3-diotahydro-iotasoiotandol-l-one[00356] 5-Bromo-2,3-dihydro-isoindol-l-one (230mg, 1 08mmol), bis(pmacolato)diboron(300mg, 1 18mmol), PdCl2dppf (25mg, 31 mol) and KOAc (320mg, 3 26mmol) are suspended in dioxane (4mL), purged with nitrogen for 5 minutes and then heated at 850C overnight The solvent is removed in vacuo and the residue partitioned between ethyl acetate and water The aqueous layer is extracted with ethyl acetate (3x) and the combined organic phases are washed once with brine, filtered through MgStheta4 and evaporated The solid residue is triturated with hexane and dried in vacuo to yield the title compound (185mg, 66 %) as a grey solid 1H-NMR (400MHz, CDCl3) delta ( pp)pl 37 (12H, s), 4 45 (2H, s), 6 38 (IH, br s), 7 87 (IH, d), 7 93 (2H, m)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
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