Category: 6941-75-9

Reference 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: Toa solution of 4a (10.0 g, 35.3 mmol)in MeOH (200 mL) was added 8M KOH solution (20 mL) and then heated to reflux.After 36 h, the reaction mixture was concentrated under reduced pressure.The mixture was diluted with H2O (100 mL), extracted with EA (75 mL×2), dried over Na2SO4 and concentrated under reducedpressure. The residue was dissolved in THF (100 mL). Di-tert-butyldicarbonate (9.0 g, 41.2 mmol) and DMAP (0.5 g, 4.0 mmol) was added and thenthe reaction mixture was stirred at room temperature for 4 h. Afterconcentration, the residue was purified by silica gel column chromatography(PET/EA = 15:1, v/v) to affordcompound 5a as colorless oil (8.3 g,75.5%).

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

Reference:
Article; Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3050 – 3056;,
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Reference 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.

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 RT. 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.

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

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
Indoline – Wikipedia,
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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. Product Details of 6941-75-9

Preparation of 5-bromo-2,3-dihydro-1H-isoindole (13); 564.2 ml of a 1M borane/THF solution are added dropwise to 42.5 g (188 mmol) of 5-bromoisoindole-1,3-dione in 300 ml of THF (dry) at -5 C. over a period of 60 min. The mixture is subsequently stirred for 2 h at 22 C. and then for 16 h at 80 C. The mixture is then cooled to 0 C., before 200 ml of methanol (exothermic.) and 200 ml of 2M hydrochloric acid are slowly added. The resultant mixture is stirred for 3 h at 80 C., cooled to 22 C., and 100 ml of water are added. The aqueous solution is extracted three times with 150 ml of dichloromethane each time, dried over sodium sulfate, filtered and evaporated to dryness: 5-bromo-2,3-dihydro-1H-isoindole; yield 15.4 g of ?13? (41.3%); MW 198.06; Rt 1.099 min (?polar? method).

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

Reference:
Patent; Merck Patent Gesellschaft Mit Beschrankter Haftung; US2010/311745; (2010); A1;,
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Reference of 6941-75-9, 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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of LIALH4 (8.8 mL of 1 M solution in Et20, 8.8 mmol) in dry THF (13 mL) was cooled to 0 C. Concentrated H2S04 (0.42 g, 4.3 mmol) was added dropwise, and the resulting mixture was stirred at 0 C for 30 min. 5-Bromo-lH-isoindole-1, 3 (2H)- dione (0.409 g, 1. 81 mmol) was added in portions over 15 minutes, and the reaction was allowed to warm to room temperature when the addition was complete. The reaction was stirred at room temperature for 2. 5H, and then cooled back to 0 C and quenched by the addition OF MEOH (2 mL). Et2O was added (50 mL), followed by NA2S04-10H20. The mixture was stirred vigorously until the organic layer was clear. The mixture was then filtered and concentrated in VACUO. Purification by column chromatography (4: 1 CH2CL2; MeOH + 0. 1% conc. NH3) provided the title compound (0.128 g, 36%). 1H-NMR (CDCl3): No. 7.38 (s 1H), 7.33 (D,@ J=7. 6 Hz, 1H), 7.12 (d, J=8. 0 Hz, 1H), 4.21 (s, 2H), 4.17 (s, 2H), 2.09 (s, 1H). MS (ESI) (M+H) +=198/200.

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; ASTRAZENECA AB; WO2004/60882; (2004); A1;,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromoisoindoline-1,3-dione

To a solution of hydroxyproline tripeptide precursor (200 mgs, 0.359mmol) in 4 mL of DMF at room temperature was added 4-bromophthalimide(97 mgs, 0.430 mmol) and triphenyl phosphine (206 mgs, 0.789 mmol).Sonicate until dissolved and add DIAD (152 uL, 0.789 mmol). Stir at roomtemperature overnight. Remove solvent under reduced pressure and extractwith ethyl acetate and water. ‘Separate the layers and dry over MgSCu, filterand strip. Purify using silica gel chromatography eluting (10 -100% ethylacetate in hexane). Further purify on reverse phase HPLC (ACN/Water) toafford 102 as a white solid (98 mgs, 36%). 1H NMR (300 MHz, CDCls): 5 7.95(s, 1H), 7.88 (d, J=7.9 Hz, 1H), 7.71 (d, J= 7.7 Hz, 1H), 7.65 (s, 1H), 7.43 (s, 1H),6.03 (m, 1H), 5.37 (d, J= 15.5 1H), 5.31-5.07 (bs, 5H), 4.91 (m, 1H), 4.77 (m, 1H),4.23-4.03 (bs, 7H), 3.81 (t, J= 7.9Hz, 1H), 2.75 (m, 2H), 2.01 (m, 1H), 1.68-1,50(bs, 8H), 1.30 (q, J= 7.0 Hz, 6H), 1.10 (s, 1H), 0.99 (s, 9H). 31P NMR (300 MHz,CDCls): 8 22.92 (s, IP), 22.75 (s, IP). LC/MS: 766 (M++ 1).

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

Reference:
Patent; GILEAD SCIENCES, INC.; WO2006/20276; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

General procedure: A mixture of 2-(7-methoxynaphthalen-1-yl)ethanamine (compound 3, 101 mg, 0.5 mmol), sodium acetate (82 mg, 1.0 mmol) and cyclic anhydrides 1.0 mmol) in 5mL acetic acid was heated to reflux for 3 h in a round bottomed flask. After the completion of reaction (as evidenced by TLC), the resulting mixture was concentrated under reduced pressure and washed with ethyl acetate (10 mL×3), then the concentrated organic layer was purified by column chromatography on silica gel to obtain pure product.

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

Reference:
Article; Chang, Ying; Pi, Weiyi; Ang, Wei; Liu, Yuanyuan; Li, Chunlong; Zheng, Jiajia; Xiong, Li; Yang, Tao; Luo, Youfu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1672 – 1676;,
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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. COA of Formula: C8H4BrNO2

280 ml of 1M 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 0 C. then heated at reflux overnight. The reaction was cooled to 0 C. then treated cautiously with methanol (100 ml) followed by 2M HCl (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 (×3). The aqueous was basified with 2M NaOH then extracted with DCM (×3). 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 (1H, d), 7.20 (1H, d), 4.05 (4H, s).

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; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
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Related Products of 6941-75-9, 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 6941-75-9 as follows.

As an example of a synthesis method of core Formula VIi-VIj, 4-bromophthalimide(25) can be treated with a reducing agent (e.g., BF OEt followed by BH THF) in an appropriate solvent (e.g., tetrahydrofuran, THF) for the appropriate length of time at the appropriate temperature, to yield 4-bromoisoindoline, 26. The appropriate temperature and appropriate length of time are determined by referenece to Houben-Weyl 4th Ed. 1952, Methods of Organic Synthesis, Thieme, Volume 21.; 5-bromoisoindoline-l,3-dione (5 g, 22.1 mmol) is dissolved in anhydrous THF (30 ml), treated with BF3 OEt2 (6.667 ml, 132.7 mmol) is added and the reaction was stirred at ambient temperature for 30 minutes. To the reaction mixture 1.0M BH3 THF complex (176.94 ml, 525.3 mmol ) is added and the reaction is heated to 4O0C for 36 h. The progress of the reaction is followed by LC/MS. After completion, the reaction mixture is cooled to ambient temperature and quenched with MeOH (6 ml, drop wise) until the bubbling ceases. Then 2N HCl in water (-40 ml, 80 mmol) are added and the mixture is refluxed for 3 h. The reaction is then cooled to ambient temperature and is washed with diethyl ether (2 x 40 ml). The water layer is brought to pH 14 with 6N NaOH (aq) and extracted with ethyl acetate (3 x 100 ml). The combined organic extracts are dried over anhydrous Na2Stheta4 and solvent is removed under reduced pressure to yield 5-bromoisoindoline (68%), (m/z 413[MH+]).

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.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 6941-75-9

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-l,3-dione (5 g, 22mmol) 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 RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HC1. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2S04 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 258-261C; 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.

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

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William, C.; HUNTER, James, E.; WATSON, Gerald, B.; PATNY, Akshay; IYER, Pravin, S.; BORUWA, Joshodeep; WO2014/100206; (2014); A1;,
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. Computed Properties of C8H4BrNO2

5-bromoisoindoline-1,3-dione (2.73 g, 12.1 mmol)Was suspended in tetrahydrofuran (20 mL)To this was added borane-tetrahydrofuran (1 M, 48 mL).The reaction was refluxed overnight and cooled to 0 C,Followed by methanol (30 mL),2M hydrochloric acid (30 mL).The mixture was refluxed for 2 hours,Cooled to room temperature and concentrated under reduced pressure.The residue was partitioned between dichloromethane(50 mL) and water (50 mL). The separated aqueous phase was washed with dichloromethane (50 mL x 2) and adjusted to pH with 1 M sodium hydroxide solutionTo 11 and extraction with dichloromethane (80 mL x 4). The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure,The crude product was obtained as a dark brown oil (1.3 g, 54%),The product was purified and used directly in the next step.

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
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