Category: 6941-75-9

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, name: 5-Bromoisoindoline-1,3-dione

Sodium borohydride (3.48 g, 92.0 mmol) was added to the solutionof 5-bromopthalamide (2.0 g, 8.8 mmol) in THF, and theresultant suspensionwas cooled to 10 C. Then, BF3.Et2O (12.7 mL,102.6 mmol) was added slowly and the reaction mixture wasrefluxed. After 24 h, the reaction mixture was allowed to cool to0 C and cold H2O (18 mL) was added. EtOAc (100 ml) was addedand the reaction mixture was made alkaline using 6.0 M aqueousNaOH. The organic layer was separated and concentrated using arotary evaporator. The residue was diluted with Et2O (50 mL) andacidified to pH 2. The aqueous layerwas separated, made alkaline topH 10 using 6.0 M aqueous NaOH and extracted with EtOAc(70 mL). The organic layer was separated, washed with brine(3 70 mL), dried (Na2SO4) and concentrated using rotary evaporatorto yied the 5-bromo-isoindoline (47). The residue was used infurther reactions without purification.

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Reference:
Article; Ojha, Ritu; Nepali, Kunal; Chen, Chun-Han; Chuang, Kuo-Hsiang; Wu, Tung-Yun; Lin, Tony Eight; Hsu, Kai-Cheng; Chao, Min-Wu; Lai, Mei-Jung; Lin, Mei-Hsiang; Huang, Han-Li; Chang, Chao-Di; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 190; (2020);,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H4BrNO2

To a solution of 4a (10 g, 44.4 mmol) in TRF (200 mE) was added NaI3R4 (17.6 g, 464.8 mmol), followed by 13F3.Et20 (170 ml, 519.2 mmol) drop- wise at room temperature. The mixture was then heated at 80 C. overnight, cooled to 0 C. and adjusted to pH 13 with aqueous NaOH solution. The mixture was extracted with ethyl acetate (100 mEx3). The combined organic phase was washed with water, brine and dried over anhydrous Na2504. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (DCM:MeOR=10:1, v: v) to provide 4b (7.3 g, 83% yield). EC-MS: 198 [M+1].

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; HELSINN HEALTHCARE SA; Giuliano, Claudio; Daina, Antoine; Pietra, Claudio; (254 pag.)US2017/275301; (2017); A1;,
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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. SDS of cas: 6941-75-9

Synthesis of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) A solution of 1, 2-dibromoethane (20 ml, 230.35 mmol) in ether/benzene (270 ml/100 ml) was added to a stirred suspension of magnesium turning (8.64 g, 355.6 mmol) in ether (100 ml). The reaction was stirred at room temperature for 2 h. To this was added a solution of n-butyllithium (110 ml, 177.6 mmol) and 3-bromothiophene (2, 29 g, 177.6 mmol) in tetrahydrofuran (200 ml) (prepared at -78 C.) and the reaction was stirred at room temperature for 1 h. Then a solution of 4-bromophthalimide (1, 4 g, 17.7 mmol) in dichloromethane (50 ml) was added and the reaction was stirred at room temperature for 1 h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. ammonium chloride and extracted with dichloromethane. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified on combiflash using 25% ethyl acetate in hexane to afford mixture of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.97 g, crude; MS (ESI) m/z 307.95 [M-1]-.

The synthetic route of 6941-75-9 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.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Related Products of 6941-75-9, A common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 4-bromophthalic anhydride (25 g) in formamide (75 ml) was heated at 2000C for 16 hours then allowed to cool to room temperature. The reaction mixture was diluted with water (200 ml), filtered, the filter cake was washed with water then diethyl ether and sucked dry to give 20.85 g of light mustard solid.280 ml of 1 M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at O0C then heated at reflux overnight. The reaction was cooled to O0C then treated cautiously with methanol (100 ml) followed by 2M HCI (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (x3). The aqueous was basified with 2M NaOH then extracted with DCM (x3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1 H1 d), 7.20 (1H, d), 4.05 (4H, s).

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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 a suspension of 5-bromo-1 H-isoindole-1 ,3(2H)-dione (ABCR, 5.Og) and triphenylphosphine (8.7Og) in tetrahydrofuran (THF) (10OmL) under nitrogen at room temperature was added di-t-butyl azodicarboxylate (7.64g). The suspension was cooled in an ice/water bath and to this was added iso-propanol (2.032 ml_). The reaction mixture was allowed to warm to room temperature to give a pale yellow solution. After 60 minutes, the solvent was removed in vacuo and the residue was dissolved in DCM (3OmL). This was applied to a 75Og silica cartridge and eluted with a gradient of 0-40% ethyl acetate in cyclohexane over 8CV. The required fractions were combined and evaporated in vacuo to give the title compound (5.27g) as a pale yellow solid.1H NMR (CDCI3): 7.95 (1 H, d, J=1.5Hz), 7.84 (1 H, dd, J=1.5, 8Hz), 7.68 (1 H, d, J=8Hz), 4.53 (1 H, heptet, J=7Hz), 1.49 (6H, d, J=7Hz)

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

Reference:
Patent; GLAXO GROUP LIMITED; JIN, Qi; WO2010/102968; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Safety of 5-Bromoisoindoline-1,3-dione

4-bromo phthalimide (manufactured by Tokyo Kasei Kogyo) 9.95 g (44.0 mmol) were placed in a two-necked eggplant flask 50ml was replaced with nitrogen gas.Then added iodine 5.87g (23.1mmol) and 10% fuming sulfuric acid (Yotsuhata Chemical Industry Co., Ltd.) 12ml, it was subjected to 23 hours of reaction at 90C .The reaction mixture was poured into ice cooled to room temperature, filtered through a glass filter, to give a yellow solid 12.8 g. The resulting solid was dissolved in concentrated sulfuric acid 35 ml, the reaction was carried out for 5 hours at 130C..The reaction mixture was ice-cooled, and filtered the solid precipitated by adding ice water to give a solid 13.8g of phthalic acid derivatives. Next, the resulting solid was dissolved at room temperature sodium hydroxide 3.6g aqueous solution dissolved in water 18 ml. The basic aqueous solution of acetic acid was added to adjust the pH to 3-4, filtered the white precipitate of the mono sodium salt of the phthalic acid derivative precipitated. The resulting white solid was suspended in water, to pH 1 or less with concentrated hydrochloric acid to give a white solid 6.45g again as phthalic acid derivatives. The solid was dissolved in toluene 48 ml, was added acetic anhydride 8.7g (85.7mmol), the reaction was carried out for 4 hours at 105C. To give a white solid 5.87g The reaction mixture was concentrated under reduced pressure.The solid was purified by recrystallization in toluene to give 4-bromo-5-iodo-phthalic anhydride object 5.13g of (14.5mmol) (33% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; Tosoh Corporation; Watanabe, Masato; Ohashi, Tomokazu; Fujita, Takumi; (137 pag.)JP5716821; (2015); B2;,
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Application 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 38 Preparation of Ethyl 2-(1-oxo-6-vinylphthalazin-2(1H)-yl)acetate (BI24) Step 1. 5-Bromo-3-hydroxyisoindoline-1-one (BI25) A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C. for 30 min and 3 h at ambient temperature. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261 C.; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]-); IR (thin film) 1684, 3246, 606 cm-1.

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; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
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Application 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.

To a suspension of 5-bromoisoindoline-l,3-dione (2.73 g, 12.1 mmol) in THF (20 mL) was added Borane-THF complex (1 M, 48 mL). The reaction was heated at reflux overnight, then cooled to 0 C, and treated with MeOH (30 mL), followed by 2 M HCI (30 mL). The mixture was heated at reflux for 2 h, then cooled to rt and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and H20 (50 mL). The separated aqueous phase was washed with DCM (50 mL x 2), then adjusted to pH 11 with 1 M NaOH (6 mL), and extracted with DCM (80 mL x 4). The combined organic phases were dried over anhydrous a2S04, filtered and concentrated in vacuo to give the crude product as dark brown oil (1.3 g, 54%), which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 198.0 [M + H]+.

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

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
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Synthetic Route 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.

To a stirring room temperature solution of 4-bromophthalimide (1.02 g, 4.51 mmol) in dimethylformamide (20 mL) add 60% sodium hydride (0.235 g, 5.87 mmol). Stir this mixture at ambient temperature for 15 minutes and then add iodomethane (0.628 mL, 10.09 mmol). Stir the reaction for 30 minutes at ambient temperature then quench it with brine. Extract the resulting aqueous mixture with ethyl acetate. Wash the combined extracts with brine; dry (sodium sulfate) and concentrate them in vacuo. Purify the resulting material on a flash column (silica gel; 70%-100% CH2C12 gradient in hexanes) to obtain the title compound, 0.960 g (89%). MS (IS+) 7nle 240 (M + H’79Br), 242 (M + H, “Br).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
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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.

280 ml of 1 M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at O0C then heated at reflux overnight. The reaction was cooled to 00C then treated cautiously with methanol (100 ml) followed by 2M HCI (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (x3). The aqueous was basified with 2M NaOH then extracted with DCM (x3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1 H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1 H, s), 7.36 (1H, d), 7.20 (1 H, d), 4.05 (4H, s).

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; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem