Category: 552330-86-6

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.

General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0¡ãC. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0¡ãC for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10percent acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80percent). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J? 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

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; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 552330-86-6, 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. 552330-86-6 name is 5-Bromoisoindolin-1-one, 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.

(6-(1-(and 2-)(4-methoxybenzyl)-2H-tetrazol-5-yl)-4?-methyl-5-sulfamoyl-[1,1?-biphenyl]-3-yl)boronic acid (40 mg, 0.083 mmol) and 6-bromoisoindolin-1-one (19.47 mg, 0.092 mmol) was suspended in ethanol (835 mul) and potassium phosphate tribasic (250 mul, 0.250 mmol). The reaction mixture was sparged with N2 for 5 min. 1,1?-bis(di-tert-butylphosphino)ferrocene palladium dichloride (5.44 mg, 8.35 mumol) was added and the reaction mixture microwaved at 110 C. for 90 min. The crude reaction mixture was diluted with EtOAc and water. The aqueous phase was extract with EtOAc (×2), then the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The reaction mixture was purified by reverse phase HPLC on a C18 column and then eluted with 10% to 100% MeCN in water. The major UV active material was lyopholized to provide a white solid that was utilized directly in the deprotection. LC-MS: calculated for C30H26N6O4S 566.2; observed m/e: 467.5 (M+H)+.

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.

Related Products 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.

5-Bromo-2,3-dihydro-isoindol-l-one (leq) was added to a solution of benzyl bromide (l . l eq) and K2CO3 (2eq) in DMF under N2. The mixture was stirred at rt for 16 hrs. Reaction was diluted in water and the compound precipitated. The solid was filtered and dried under reduced pressure. Compound was used in the next step without further purification.

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

Application of 552330-86-6, 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. 552330-86-6 name is 5-Bromoisoindolin-1-one, 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.

To a stirring solution of 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid(compound 301) (400 mg, 1.88 mmol) in dimethylformamide (10 mL) under nitrogen atmosphere, were added cesium carbonate (1.8 g, 5.66 mmol),tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.09 mmol) and 5-bromoisoindolin- 1-one (913 mg, 3.77 mmol) and the resultant reaction mixture was heated to 90 C for 6 h. The reaction mixture was filtered off and the filtrate was extracted with ethyl acetate (3 x). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification was done by column chromatography (silica gel, 0-3% methanol in dichloromethane) afforded 5-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isoindolin-l-one as a solid.

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.

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., Quality Control of 5-Bromoisoindolin-1-one

In a screw cap vial under an argon atmosphere 3,4-dimethoxy-2- (isobutoxy)phenylboronic acid (Compound 302) (0.015g, 0.06mmol) and the bromide (0.066 mmol) was dissolved in dimethoxyethane (0.35 mL). K2C03 (1M solution, 0.12 mL, 0.12 mmol) and Pd(PPh3)4 (0.004g, 0.003mmol) was added. The suspension was shaken at 80C for 72h. Brine (2 mL) was added and the mixture was extracted with CH2CI2 (3 mL). The phases were separated using a phase separation cartridge (Chromabond, PTS) . The organic phase was concentrated in vacuo and the residue was dissolved in DMF (0.3 mL) and purified by preparative HPLC/MS.Compounds 174 – 176 were prepared according to this procedure: -i2-Isobutoxy-3r4-dimethoxy-phenyl)-2,3-dihydro-isoindol-l-one iCompound 174)1H NM (600 MHz, DMSO-SPE) delta 8.53 (s, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.64 (s, 1H), 7.56 (dd, J = 7.9, 1.2 Hz, 1H), 7.09 (d, J = 8.6 Hz, 1H), 6.93 – 6.88 (m, 1H), 4.39 (s, 2H), 3.84 (s, 3H), 3.79 (s, 3H), 3.48 (d, J = 14.4 Hz, 2H), 1.78 – 1.67 (m, 1H), 0.75 (d, J = 6.7 Hz, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes 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. Product Details of 552330-86-6

5-Bromo-2-methylisoindolin-1-oneTo a solution of 5-bromoisoindolin-1-one (2500 mg, 11.79 mmol) in DMF (20 mL) under nitrogen, at 0 °C, was added NaH (566 mg, 14.15 mmol) and the mixture was stirred for 30 min. After which, Mel (0.885 mL, 14.15 mmol) was added dropwise and the mixture was stirred at 0 °C for 2 h. The reaction was quenched with sat. aqueous NH4CI, and extracted with EtOAc (3 x 30 mL). The organic layer was washed with brine, dried and concentrated to afford 5-bromo-2-methylisoindolin-1-one (2500 mg, 7.30 mmol, 61.9 percent yield). LC-MS: m/z 226 (M+H)+1.02 min (ret. time).

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

Application of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

5-Bromo-2-methylisoindolin-1-oneTo a solution of 5-bromoisoindolin-1-one (2500 mg, 11.79 mmol) in DMF (20 mL) under nitrogen, at 0 C, was added NaH (566 mg, 14.15 mmol) and the mixture was stirred for 30 min. After which, Mel (0.885 mL, 14.15 mmol) was added dropwise and the mixture was stirred at 0 C for 2 h. The reaction was quenched with sat. aqueous NH4CI, and extracted with EtOAc (3 x 30 mL). The organic layer was washed with brine, dried and concentrated to afford 5-bromo-2-methylisoindolin-1-one (2500 mg, 7.30 mmol, 61.9 % yield). LC-MS: m/z 226 (M+H)+1.02 min (ret. time).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, name: 5-Bromoisoindolin-1-one

(i) (S)-tert-Buty l-(l-amino-3-(4-(l-(difluoromethyl)-6-oxo-l,6-dihydropyridin-3- yl)phenyl)-l-oxopropan-2-ylcarbamoyl)cyclohexylcarbamatePotassium carbonate (178 mg) in water (5 mL) was added to (S)-tert-butyl l-(l-cyano-2-(4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (Example 23 step (i), 300 mg), 5-bromoisoindolin-l-one (141 mg) and 1,1 bis(di-tert- butylphosphino)ferrocene palladium dichloride (12 mg) in degassed acetonitrile (15 mL) at 20C under an atmosphere of nitrogen. The resulting solution was stirred at 90C for 4h. The reaction mixture was concentrated to dryness and the residue purified by chromatography on silica eluting with ethyl acetate to afford the sub-titled compound (180 mg) as a colourless solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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.

To a solution of 5-bromo-2,3-dihydro-isoindol-l-one (1 equiv) in dry dioxan (0.1 M) were added bis(pinacolato)diboron (1.1 equiv), potassium acetate (3.5 equiv) and dppf (0.05 equiv). The reaction mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added to the reaction mixture, which was degassed for a further 5 minutes. The reaction mixture was heated to 70C for 2 hours under nitrogen then heated to 120C for 16 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic phases dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 and hexane was added. The resulting suspension was filtered and the collected brown powder was dried and used without further purification.5-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-l-one: (94 % yield, 76 % purity, main impurity being the boronic acid 13 %) m/z (LC-MS, ESP): 260.4 [2M+H]+ R/T = 3.51 min

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; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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., category: indolines-derivatives

A solution of 5-bromoisoindolin-1-one (2.0 g, 9.4 mmol) , N, N-dimethylpyridin-4-amine (0.23 g, 1.9 mmol) and di-tert-butyl dicarbonate (2.47 g, 11.3 mmol) in DMF (20 ml) was stirred at ambient temperature for 2 h. Water (100 mL) was then added and the mixture was extracted with EtOAc (3×30 mL) . The combined organic fractions were washed with brine (3×10 mL) , dried (Na2SO4) , filtered and the solvent evaporated under reduced pressure. The residue was purified by chromatography on SiO2(1-90EtOAc/isohexane) to give tert-butyl 5-bromo-1-oxoisoindoline-2-carboxylate. MS (EI) calc?d for C13H15BrNO3[M+H]+, 312 found, 312.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem