Tag: M.W=200-300

Related Products of 883-44-3, 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 883-44-3 as follows.

INTERMEDIATE 3; 3-(fert-Butyldimethylsilanyloxy)propylamine; To a solution of N-(3-hydroxypropyl)phthalimide (5.25 g, 24.36 mmol) in DMF (20 niL) was added imidazole (16.6 g, 240 mmol) and tert-butyldimethylsilyl chloride (19 g, 120 mmol). The reaction was stirred at room temperature for 18 hours before the volatiles were removed in vacuo and a portion of the crude product was subjected to column chromatography (SiO2, 1:1 DCM/hexanes) to give 2-[3-(tert-butyldimethyl- silanyloxy)propyl]isoindole-l,3-dione as a clear oil (5 g). 2-[3-(tert-Butyldimetliyl- silanyloxy)propyl]isoindole-l,3-dione (5 g, 26.4 mmol) was dissolved in ethanol (50 ml) and methyl hydrazine (2.94 ml, 55.4 mmol) added. The reaction was heated to 75C for 8 hours before concentration in vacuo. The crude residue was triturated with a mixture of diethyl ether (150 mL) and hexanes (50 niL) and the resultant solid removed by filtration. The solvents were removed in vacuo to give the title compound as a pale yellow oil (1.8 g, 61%). deltaH (DMSOd6) 4.58 (2H, br s), 3.63-3.58 (2H, m), 2.67-2.62 (2H, m), 1.60-1.55 (2H, m), 0.83 (9H, d, J 1.1 Hz), 0.00 (6H, d, J 1.2 Hz). LCMS (ES+) RT 1.77 minutes, 190 (M+H)+.

According to the analysis of related databases, 883-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2007/88345; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-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 5181-35-1, Formula: C10H8BrNO3

(2) to 120mmol of compound III in 10mL of glacial acetic acid solution was added 15mL of 48% by weight of hydrobromic acid, stirred at 130 C for 5 minutes, cooled, filtered, the filtrate was concentrated to give a yellow compound IV

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; Nanjing Tech University; Hu Xuhong; Li Song; (13 pag.)CN109678810; (2019); A;,
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Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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. SDS of cas: 169037-23-4

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(p-chlorophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-chlorophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5f): Melting point 259-261 C; white solid, 95%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.60 (d, J = 13.92 Hz, 1H), 4.18-4.23 (m, 1H), 3.86 (d, J = 10.28 Hz, 1H), 3.24-3.38 (m, 2H), 2.92-3.00 (m, 2H), 2.50-2.54 (m, 1H), 2.33-2.39 (m, 1H), 6.53-6.56 (m, 2H), 6.67-7.02 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.8, 46.9, 52.3, 53.1, 61.5, 65.9, 70.7, 100.4, 109.8, 123.9, 124.1, 126.0, 128.1, 128.2, 128.4, 128.7, 128.8, 129.0, 130.4, 131.4, 132.5, 132.6, 135.8, 135.9, 136.4, 140.6, 143.7, 136.2, 137.6, 138.5, 139.9, 144.4, 179.1, 196.9. EI-MS: m/z 780 (M+). Anal. Calcd for C44H34Cl2F3N3O3: C, 67.70; H, 4.39; N, 5.38; Found: C, 67.59; H, 4.51; N, 5.25.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 169037-23-4, its application will become more common.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Quality Control of 6-Bromoisoindolin-1-one

Compound WX005-3 (1.00 g, 4.72 mmol, 1.00 eq), compound WXBB-1 (1.53 g, 14.15 mmol, 3.00 eq), cuprous iodide (89.82 mg, 471.61 mumol, 0.10 eq), potassium carbonate (1.96 g, 14.15 mmol, 3.00 eq), and tetramethylethylenediamine (54.81 mg, 471.61 mumol, 71.18 muL, 0.10 eq) were dissolved in toluene (10.00 mL). The mixture was purged with nitrogen three times, and then reacted at 130 C. for 16 hours under a nitrogen atmosphere. After the reaction was completed, the reaction solution was added with methanol (15 mL), and filtered, followed by concentrating of the filtrate. The crude product was separated and purified by prep-HPLC (column: Phenomenex Gemini 150*25 mm*10 mum; mobile phase: [water (0.05% HCl)-ACN]; B %: 0-30 (10 min) %-30-55 (4 min) %, 14 min). Compound WX005-4 was obtained, 1H NMR (400 MHz, METHANOL-d4) delta ppm 8.07 (s, 1H), 7.89 (s, 1H), 7.80-7.83 (m, 1H), 7.72-7.74 (m, 1H), 7.384 (s, 1H), 4.53 (s, 2H), 1.90-1.95 (m, 1H), 0.89-0.93 (m, 2H), 0.76-0.78 (m, 2H). MS m/z: 239.9 [M+H]+.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIAN COSUNTER PHARMACEUTICAL CO., LTD.; Wu, Chengde; Yu, Tao; Li, Ning; Chen, Shuhui; US2019/375728; (2019); A1;,
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Reference of 87-48-9, 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. 87-48-9, name is 5-Bromoindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 C (ice bath), whereupon sodium hydride (60% dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 C for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90%-100% yield).

The synthetic route of 5-Bromoindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jin-Yan; Wang, Hui; Yang, Yan-Li; Shen, Shou-Jie; Chen, Jian-Xin; Tetrahedron Letters; vol. 58; 27; (2017); p. 2636 – 2639;,
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Adding a certain compound to certain chemical reactions, such as: 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-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 104618-31-7, Recommanded Product: 104618-31-7

To a solution of PPh3 (1.28 g, 4.9 mmol) in THF (12 mL) was added dropwise DEAD (852 mg, 4.9 mmol) at -10 C. After the white solid was appeared, compound 2-(4-hydroxycyclohexyl)isoindoline-1,3-dione (600 mg, 2.45 mmol) was added, followed by CH3COSH (0.35 mL, 4.9 mmol) at -10 C. The mixture was stirred at room temperature overnight. TLC (PE:EA=1:1) showed the reaction was complete. The mixture was poured into water (200 mL) and extracted with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL×3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give S-(4-(1,3-dioxoisoindolin-2-yl)cyclohexyl) ethanethioate (600 mg, 81%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Tolero Pharmaceuticals, Inc.; Xu, Yong; Brenning, Benjamin Gary; Kultgen, Steven G.; Liu, Xiaohui; Saunders, Michael; Ho, Koc-Kan; (119 pag.)US9416132; (2016); B2;,
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Application of 104618-31-7, These common heterocyclic compound, 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-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 mixture of 7-bromoquinoxalin-5-ol (47.53 g, 211.2 mmol), 2-(4- hydroxycyclohexyl)isoindoline-l,3-dione (52.41 g, 213.7 mmol), and PPh3 (87.31 g, 332.9 mmol) in THF (740 mL) at 21 C was added tert-butyl (NZ)-N-tert- butoxycarbonyliminocarbamate (DTBAD) (79.51 g, 328.0 mmol) in portions over 40 min so as to maintain the temperature below 30 C and the resultant reaction mixture was stirred at room temperature for a further 20 h. The reaction was evaporated in vacuo. The residual reddish-brown viscous oil was dissolved in CH2C12 and filtered through a plug of silica in a glass column using applied air pressure (plug was made with 1L of dry silica suspended in CH2C12). The plug was eluted with CH2C12, the fractions were combined and evaporated in vacuo to afford a red-brown viscous oil/foam, that was then dissolved in 700 mL of MeOH before precipitating. The mixture was stirred at room temperature for 1 h, filtered, washed with cold MeOH (500 mL) and Et20 (100 mL), then dried in vacuo to yield a tan solid that was suspended in 300 mL MeOH and brought to reflux for 10 min. The suspension was cooled to room temperature and filtered, washed with a further MeOH and Et20 (4: 1), and dried in vacuo to provide 2-[4-(7- bromoquinoxalin-5-yl)oxycyclohexyl]isoindoline-l,3-dione (58.43 g, 126.6 mmol, 59.94%). 1H NMR (400 MHz, CDC13) d 8.96 (d, J = 1.8 Hz, 1H), 8.86 (d, J = 1.8 Hz, 1H), 7.91 (d, J = 1.9 Hz, 1H), 7.89 – 7.82 (m, 2H), 7.78 – 7.67 (m, 2H), 7.30 (d, J = 1.9 Hz, 1H), 4.95 (s, 1H), 4.29 (tt, J = 12.5, 3.7 Hz, 1H), 2.87 (qd, J = 13.1, 3.5 Hz, 2H), 2.44 (d, J = 15.2 Hz, 2H), 1.80 (t, J = 14.1 Hz, 2H), 1.67 (d, 2H). ESI-MS m/z calc. 451.05316, found 452.19 (M+l)+; Retention time: 0.92 minutes.

Statistics shows that 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 104618-31-7.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WEINBERG, Marc, Saul; D’ASTOLFO, Diego, Sebastian; MAHAJAN, Sudipta; (258 pag.)WO2019/143675; (2019); A1;,
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Reference of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 38), (lH-tetrazol- 5-ylmethyl)-carbamic acid tert-butyX ester (7.66 g, 74 mmol, prepared as per procedure described in step 2 of preparation 19) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at 25 C. After 16 hours, the reaction mixture was filtered and filtrate was slowly poured into chilled water (700 ml) and stirred for 30 minutes. The precipitated compound was filtered and washed with water (100 ml). The solid compound was dried at 35C for 2 hours under high vacuum, to provide 16 g of tert-butyX [(2-{2-[(l,3-dioxo- l,3-dihydro-2H- isoindol-2-yl)oxy]ethyl}-2H-tetrazol-5-yl)methyl] carbamate in 55% yield. Analysis: Mass: 389.4 (M+l); for Molecular weight: 388 and Molecular formula: Ci7H20N6O5.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Bromoethoxy)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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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. category: indolines-derivatives

To a solution of 4-bromophthalimide (22.6 g, 100 mmol) in dried tetrahydrofuran (250 mL) was added dropwise borane-dimethyl sulfide complex (51 mL, 500 mmol), stirred at room temperature for 2 hours, and then refluxed overnight. After cooling, methanol was carefully added dropwise to quench the excess borane. The resulting mixture was evaporated and concentrated, and then the residue was purified by silica gel column chromatography to give 5-bromoisoindoline (10.36 g). Yield: 52%. MS m/z[ESI]: 198.0[M+1].

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; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); A1;,
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Reference of 954-81-4, 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. 954-81-4, name is N-(5-Bromopentyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained. 2-(5-(Pyrrolidin-1-yl)pentyl)isoindoline-1,3-dione (1) [55]. Procedure M1. Reaction of 2-(5-bromopentyl)isoindoline-1,3-dione [37] (0.5 g, 1.69 mmol) with pyrrolidine (0.13 g, 1.86 mmol) and K2CO3 (0.7 g,5.1 mmol) in acetonitrile (25 mL), after 20 h, column chromatography gave oil product. Yield 0.35 g(73%). TLC (S3) Rf = 0.13. MW 286.17. Formula: C17H22N2O2. MS: m/z 287.28 [M + H]+. 1H-NMR(300 MHz, CDCl3) delta ppm: 7.89-7.77 (m, 2H), 7.78-7.65 (m, 2H), 3.69 (t, J = 6.9 Hz, 2H), 3.00 (m, 4H),2.06-1.88 (m, 4H), 1.81-1.65 (m, 4H), 1.48-1.21 (m, 4H). Hydrochloride salt: M.p. 190C. Elementalanalyses (%) for C17H22N2O2 HCl Calc. C 63.25; N 8.63; H 7.18, found: C 62.73; N 8.54; H 7.27.

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, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
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