Category: 337536-15-9

Adding a certain compound to certain chemical reactions, such as: 337536-15-9, name is 4-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 337536-15-9, Recommanded Product: 4-Bromoisoindolin-1-one

A mixture of the 4-bromo-2, 3-dihydro-isoindol-1-one (0.159 g, 0.749 mmol), di tert butyl dicarbonate (0.33 g, 1.5 mmol), triethylamine (0.11 ml, 0.75 [MMOL)] and DMAP (0.092 g, 0.75 [MMOL)] in dichoromethane (7 ml) was stirred at room temperature under nitrogen for 18 hours. The yellow solution was purified by flash chromatography on silica gel eluting with a solvent gradient of heptane/ethyl acetate (3: 1) to give the title compound (0.23 g, 99 %) as a colourless residue. [‘H-NMR] (400 MHz, [CDCI3)] : J = 1.6 (s, 9H), 4.64 (s, 2H), 7.4 (t, [1H),] 7.74 (d, [1H),] 7.84 (d, [1H).] LRMS (Electrospray) : m/z [M+ 2H + Na] [+] 336. Microanalysis : Found: C, 50.45 ; H, 4.72 ; N, 4.38. C13H14NO3Br requires C, 50.02 ; H, 4.52 ; N, 4.49%.

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Electric Literature of 337536-15-9, 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. 337536-15-9, name is 4-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(a) To a solution of 4-bromoisoindolin-l-one (106 mg, 0.5 mmol) in acetonitrile were added K2C03(110 mg, 0.8 mmol) and ethyl 2-bromoacetate (52 muEpsilon, 0.5 mmol). The mixture was refluxed overnight. The solvent was evaporated off, and the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification through flash chromatography on silica gel eluted with 8% menthol in methylene chloride gave ethyl 2-(4-bromo-l-oxoisoindolin-2-yl)acetate 150 mg as a brown gel, yield: 100%. LC/MS: (ESI) [M+H]+= 300.4

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, 4-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF WASHINGTON; FAN, Erkang; ZHANG, Zhongsheng; HUANG, Wenlin; BUCKNER, Frederick S.; (180 pag.)WO2018/237349; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 337536-15-9, name is 4-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. Recommanded Product: 337536-15-9

Carbon monoxide (g, 10 atm) was introduced into a 250-mL pressure tank reactor charged with a solution of 4-bromoisoindolin-l-one (3.0 g, 14.2 mmol), sodium acetate (2.32 g, 28.3 mmol), and Pd(dppf)Cl2 (517 mg, 0.71 mmol) in methanol (150 mL). The resulting solution stirred for 24 h at 100 C and was then cooled to room temperature. The resulting solution was concentrated under vacuum and the residue was diluted with 50 mL of water and extracted with 3×50 mL of ethyl acetate. The combined organic phases were washed with 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 1)) to afford methyl l-oxoisoindoline-4-carboxylate (2.08 g, 77%) as a light brown solid. 1H- NMR (DMSO, 300 MHz) d (ppm): 8.75 (s, 1H), 8.15 (d, J = 7.5Hz, 1H), 7.94 (d, J = 7.5Hz, 1H,), 7.65 (m, 1H ), 4.60 (s, 2H), 3.89 (s, 3H). MS: (ESI, m/z): 192[M +H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 337536-15-9, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

337536-15-9, name is 4-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 4-Bromoisoindolin-1-one

General procedure: Example 1 4-[1-(3-chloro-4-fluorophenyl)-5-(3-chloro-5-fluorophenyl)-1H-pyrazole-3-yl]-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one Step 4 [0522] 100 mg (0.25 mmol) of the product from step 3 is dissolved in 5 ml of dioxane and mixed with 75 mg (0.30 mmol) bis-pinakolato-diboron, 73 mg (0.74 mmol) potassium acetate and 12 mg (0.02 mmol) [1,1-bis-(diphenylphosphino)ferrocene]-dichloropalladium dichlormethane complex. The reaction mixture is stirred for 1 hour in the microwave at 120 C., cooled down to RT, mixed with 63 mg (0.37 mmol) of the compound from example 22A, 0.25 ml sodium carbonate solution (2 N in water, 0.50 mmol) and 10 mg (0.01 mmol) [1,1-bis-(diphenylphosphino)ferrocene]-dichloropalladium-dichlormethane complex and mixed for 2 hours at 120 C. The reaction mixture is filtered through a Millipore syringe filter, mixed with DMSO, and separated twice using preparative HPLC (solvent: acetonitrile/water gradient). This produces 42 mg (37% of theoretical yield) of the title compound. Example 3 4-[1-(3-chloro-4-fluorophenyl)-5-(3-chloro-5-fluorophenyl)-1H-pyrazole-3-yl]-2,3-dihydro-1H-isoindole-1-one [0533] [0534] The synthesis of the title compound is performed starting from 100 mg (0.25 mmol) of the product from step 3 of example 1 in a manner analogous to the synthesis of the compound from example 1. In step 4, instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindol-1-on (63 mg, 0.30 mmol) is used. The result is 74 mg (65% of theoretical yield) of the title compound. [0535] 1H-NMR (400 MHz, DMSO-d6): delta=4.72 (s, 2H), 7.21 (dt, 1H), 7.32-7.41 (m, 2H), 7.49 (s, 1H), 7.51-7.58 (m, 2H), 7.62 (t, 1H), 7.71 (d, 1H), 7.83 (dd, 1H). [0536] LC-MS (Method 1): Rt=1.28 min; MS (ESIpos): m/z=456 [M+H]+.

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AICURIS GMBH & CO. KG; Wildum, Steffen; Klenke, Burkhard; Wendt, Astrid; US2015/203500; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 337536-15-9 as follows. Computed Properties of C8H6BrNO

EXAMPLE 2A 4-bromo-7-nitro-1-isoindolinone A 0 C. solution of Example 1C (5 g, 23.6 mmol) in 10 mL sulfuric acid was treated with a solution of concentrated nitric acid (1.55 mL, 24.7 mmol) in 10 mL sulfuric acid via addition funnel. The resulting mixture was stirred at 0 C. for 1 hour, warmed to room temperature, stirred overnight, poured over ice, and filtered. The filter cake was washed with water and diethyl ether and then dried to give 5.39 g of the desired product. 1H NMR (300 MHz, DMSO-d6) delta 4.39 (s, 2H); 7.88 (d, J=8.1 Hz, 1H); 8.05 (d, J=8.5 Hz, 1H); 9.17 (s, 1H).

According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 337536-15-9,Some common heterocyclic compound, 337536-15-9, name is 4-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.

A suspension of Example 1C (10.6g, 50 mmol) and 4,4,5,5,4′,4′,5′,5 -octamethyl-[2,21bi[[l,3,2]dioxaborolanyl] (15.23g, 60 mmol) in DMF (390 mL) was stirred until a clearyellow solution was obtained. The solution was then treated with potassium acetate (14.72g,150 mmol), degassed with nitrogen, treated with [1.1 -bis(diphenylphosphino)-ferrocene]dichloropalladium [H]-CH2C12 (7g, 8.5 mmol) and heated to 90 C overnight. The(R)reaction was cooled to room temperature and filtered through diatomaceous earth (Celite ),and concentrated. The concentrate was partitioned between water and ethyl acetate and/?filtered through diatomaceous earth (Celite ). The organic phase was dried (Na2SO4),filtered, and concentrated. The crude product was purified by silica gel chromatographyeluting with 100% ethyl acetate and triturated from hexanes to give 4.56g (35% yield) of thedesired product

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/108672; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

337536-15-9, name is 4-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 4-Bromoisoindolin-1-one

Step 4: tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate To a solution of 4-bromoisoindolin-1-one (4 mmol) in THF (8 mL) was added borane-dimethyl sulfide complex (2M in THF, 14 mL) at 0 C. The reaction mixture was allowed to stir at reflux overnight and was then cooled to 0 C. The reaction mixture was quenched by the slow addition of MeOH (2 mL) and then 3N HCl. The reaction mixture was allowed to stir at reflux for 3 hr and then concentrated. Water was added to the residue and the pH of the solution was adjusted to >9 with 4N NaOH. The solution was extracted with diethyl ether. The organic solutions from this basic extraction were combined, dried over Na2SO4, filtered and concentrated to give 4-bromoisoindoline, which was dissolved in THF (5 mL). To this solution was added potassium carbonate (4 mmol) in water (0.5 mL), and BOC2O (2 mmol). The reaction mixture was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.8 mmol, 20%).

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 337536-15-9, name is 4-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. Product Details of 337536-15-9

General procedure: Step 1: A glass vial was charged with corresponding bromo-heteroaryl compound (0.20mmol, 1eq), potassium metabisulfite (88mg, 0.40mmol, 2eq), tetrabutylammonium bromide (70mg, 0.22mmol, 1.1eq), sodium formate (15mg, 0.22mmol, 1.1eq), palladium(II) acetate (5mg, 0.02mmol, 0.1eq), triphenylphosphine (16mg, 0.06mmol, 0.3eq), 1,10-phenanthroline (11mg, 0.06mmol, 0.3eq). After sealing, the vial was flushed with argon for 30min and the reagents were suspended in dry, degassed DMSO (1mL) and the reaction mixture was stirred for 4h at 70C. After cooling to RT N,N-Diisopropylethylamine (70muL, 0.40mmol, 2eq) and a solution of tert-butyl (E)-(2-aminoethyl)(3-(4-(pyridin-3-yl)phenyl)allyl)carbamate (63) (106mg, 0.30mmol, 1.5eq) in dry THF (1mL) were added and the reaction mixture was cooled to 0C. Subsequently a solution of N-bromosuccinimide (62mg, 0.40mmol, 2eq) in dry THF (1mL) was added and the reaction mixture was allowed to come to RT. After stirring for 1h the reaction was quenched by adding H2O (1mL) and brine (2mL). The resulting mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the solvent removed under reduced pressure. The residue was purified via flash-column-chromatography (SiO2, 0% to 5% MeOH in DCM) to yield the desired Boc-protected product, which was used directly in step 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 337536-15-9, its application will become more common.

Reference:
Article; Grimm, Sebastian H.; Gagestein, Berend; Keijzer, Jordi F.; Liu, Nora; Wijdeven, Ruud H.; Lenselink, Eelke B.; Tuin, Adriaan W.; van den Nieuwendijk, Adrianus M.C.H.; van Westen, Gerard J.P.; van Boeckel, Constant A.A.; Overkleeft, Herman S.; Neefjes, Jacques; van der Stelt, Mario; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 692 – 699;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 337536-15-9,Some common heterocyclic compound, 337536-15-9, name is 4-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.

A 0 C solution of Example 1C (5g, 23.6 mmol) in 10 mL sulfuric acid was treatedwith a solution of concentrated nitric acid (1.55 mL, 24.7 mmol) in 10 mL sulfuric acid viaaddition funnel. The resulting mixture was stirred at 0 C for 1 hour, warmed to roomtemperature, stirred overnight, poured over ice, and filtered. The filter cake was washed withwater and diethyl ether and then dried to give 5.39g of the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/108672; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 337536-15-9, The chemical industry reduces the impact on the environment during synthesis 337536-15-9, name is 4-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

The compound II obtained in Example 3 was dissolved in 2 L of THF. Cool down to 0 C, Sodium borohydride 2.5 eq was added in four batches. After the stirring is stable, Add boron trifluoride etherate 2.0 eq, The temperature was further raised to 70 C and refluxed for 8 hours. TLC tracking. Cool down to 0 C, The reaction was quenched by dropwise addition of methanol. Then add 6M hydrochloric acid, Adjust the pH to 3-4, The temperature was further raised to 70 C and refluxed for 8 hours. Cool to room temperature, filter, Mother liquor is concentrated, Get the product hydrochloride.

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, 4-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem