Category: 6941-75-9

Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 fuming nitric acid (9.2 mL, 0.22 mol, 1.0 eq) pre-cooled at 0 C. was added drop wise concentrated sulfuric acid (21 mL, 0.40 mol, 1.8 eq) followed by portion-wise addition of intermediate I-55 (10 g, 44 mmol, 2.0 eq) and the resulting suspension was warmed to room temperature over 1 hour and stirred for a additional 24 hours at room temperature. The crude reaction mixture was poured onto a mixture of ice and water and the solids were collected by filtration and dried in vacuo to give intermediate I-56 (11.8 g, 98%). MS (ESI): m/z 272 (M+H+).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6941-75-9, The chemical industry reduces the impact on the environment during synthesis 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Under a nitrogen atmosphere, at 0 C., to a solution of WX042-1 (5.00 g, 22.12 mmol) in tetrahydrofuran (50.00 mL) was added borane dimethyl sulfide (10 M, 11.06 mL) dropwise, and the system was stirred at 70 C. for 16 hours. After the reaction was complete, at 0 C. to the system was added 100 mL methanol to quench the reaction system. After concentration under reduced pressure, the residue was purified by column chromatography (dichloromethane:methanol=20:1) to afford Compound WX042-2 (1.00 g, 22.16% yield, 97.1% purity), white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.43 (s, 1H), 7.40-7.34 (m, 2H), 7.11 (d, J=8.5 Hz, 1H), 4.48 (d, J=16.6 Hz, 4H).

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-Bromoisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Medshine Discovery Inc.; He, Haiying; Jiang, Zhigan; Shi, Weihua; Xia, Jianhua; Li, Jian; Chen, Shuhui; US2019/375744; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-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.

Heck reaction of 4-Bromophthalic imide with 1,7-Octadien (Heck condition) 1 g 4-Bromophthalic imide (6.167 mmol), a two-fold excess 1,7-Octadien (12.33 mmol) and the catalysator system were solved in 50 ml DMF. The catalysator system consisted of Palladiumacetate (5 mol-% to Imide: 0.31 mmol), 0.92 mmol Triphenylphosphane and 6.17 mmol Triethylamin. The solution has been heated for 24 h at 150 C (Control of reaction progress via thin layer chromatography with CH2Cl2: n-Hexane [5:1]). From the resulting dark brown solution the solvent was removed by reduced pressure. The obtained viscous brown raw product was solved with 80 ml CH2Cl2 and washed three times (3 x 200 ml) with a saturated H2O/NaCl solution. After that the CH2Cl2-phase was dried with MgSO4 and the solvent was removed by reduced pressure. The viscous brown product (1) was dried under constant vacuum.Yield : quant. IR : v 1772, 1717 (s, Imide) cm-1 MS / ESI : 401.14972 m/z (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; DENTSPLY DETREY GmbH; E, Klee, Joachim; Retzmann, Nils; Ritter, Helmut; Szillat, Florian; EP2759289; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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 6941-75-9, COA of Formula: C8H4BrNO2

In a stirred three-necked reaction flask, 100 g of 4-bromophthalimide, 62 g of phenol, 92 g of potassium carbonate, 6.5 g of cuprous bromide, 7 g of N, N-dimethylglycine, 200 mL of 1,4 – dioxane, in the N2 protection, the system temperature to 85 C reaction, 24 hours after the complete reaction of the raw materials, vacuum distillation of dioxane; by adding 300mL of methylene chloride dissolved products After filtration, the filtrate was evaporated to dryness, and 100 mL of methanol was added. The temperature was raised to 40 C for 1 hour. The temperature of the system was reduced to -5 to 0 C, After stirring for 5 hours, the mixture was filtered and dried to obtain 85 g of a white crystalline solid, Yield 80% HPLC purity 98%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Lianhua Technology Co., Ltd.; Zou Benli; Xie Siwei; Yuan Li; Cui Yan; (22 pag.)CN107188875; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

Example 46 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)- phenyl)-2-(2-(5-(methylsulfonamidomethyl)-1 ,3-dioxoisoindolin-2- yl)acetoxy)ethyl)pyridine 1 -oxide (Compound 254): Scheme 46 Step 1 : Preparation of 1 ,3-dioxoisoindoline-5-carbonitrile (249): A mixture of 5-bromoisoindoline-1 ,3-dione (2.5 g, 1 1 .06 mmol) and Pd(Ph3P)4 (1 .406 g, 1 .217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1 .299 g, 1 1 .06 mmol) was added and the solution, splitted in 5 vials, was heated under microwave irradiation at 200C for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added and the organic phase was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM: MeOH = 99: 1 ) to afford 1 ,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH] +).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; CARZANIGA, Laura; LA PORTA, Elena; GUALA, Matilde; WO2013/57013; (2013); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. COA of Formula: C8H4BrNO2

5-bromo-2-ethylisoindoline-1,3-dioneTo a solution of 5-bromoisoindoline-1 ,3-dione (1 130 mg, 5 mmol) in THF (25 mL) was added iodoethane (0.606 mL, 7.50 mmol) and then slowly was added NaH (144 mg, 6.00 mmol). The resulting reaction was stirred at RT for 22 h. To the reaction mixture was added DMF (2 mL) then stirred at RT for 23 h. To the reaction mixture was added more DMF (3 mL) then was stirred at RT for 120 h. The reaction mixture was diluted with H20 (20 mL), acidified with HCI (1 mL, 1.0 N), extracted with EtOAc (3 x 20 mL), washed with brine (20 mL), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product 5-bromo-2-ethylisoindoline-1 ,3-dione (899.7 mg, 3.54 mmol, 70.8 % yield). LC-MS mlz 254.1 (M+H)+, 0.90 min (ret. time).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-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.

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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 6941-75-9, Computed Properties of C8H4BrNO2

EXAMPLE 5; Step 5A: Bromophthalimide 5a (13.0 g, 57.8 mmol) was added in six portions over 30 minutes to a stirred suspension of zinc powder (4.50 g, 69.2 mmol) and copper (II) sulfate pentahydrate (0.060 g, 0.25 mmol) in aqueous sodium hydroxide (2 M, 71 mL) at 0 C (ice-bath. ) The mixture was stirred at 0 C for an additional 30 minutes, and at room temperature for 2.5 h to complete the reaction. After filtering, the reaction solution was neutralized to pH 7 with 20% hydrochloric acid, diluted with 100 mL of ethanol, and then extracted with ethyl acetate. The extract was washed with brine, dried with MgS04 and concentrated in vacuo to afford 12.5 g (95%) of 5b as a yellow solid, LC-MS 210 (MH+-H20.)

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; NEUROCRINE BIOSCIENCES, INC.; WO2005/103039; (2005); A1;,
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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 6941-75-9

Synthetic Example 3; Synthesis of 4-bromophthalamide (hereinafter abbreviated as 4-BPA); [Show Image] 4-BPA represented by the formula (21) was synthesized from 4-bromophthalimide (hereinafter abbreviated as 4-BPI) according to the following procedure (reaction formula 3) with reference to Journal of Heterocyclic Chemistry, 1995, pp. 495-498. In a 100-ml eggplant flask, 27.8017 g (0.123 mols) of 4-BPI and 60 ml of 20% ammonia water were placed followed by reaction under stirring at 23C for 48 hours. After completion of the reaction, the reaction solution in the form of a white suspension was allowed to stand at 0C for one hour, followed by filtration under reduced pressure. The resulting white solid was dried in a reduced pressure dryer at 23C or 24 hours to obtain 29.90 g (yield: 75%) of a white powder of 4-BPA. The thus obtained white powder was subjected to identification of the structure thereof from NMR spectra and confirmed as 4-BPA. 1H-NMR (ppm/DMSO-d6):delta 7.84(s, 1H), 7.78(s, 1H), 7.67(d, 1H), 7.65(d, 1H), 7.62(d, 1H), 7.43(s, 1H), 7.40(s, 1H).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.