Category: indolines-derivatives

Related Products of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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 an oven dried flask equipped with a stir bar cooled under an inert atmosphere was added 6- nitroindoline (1.0 grams, 6.10 mmol, 0.3 M in anhydrous dichloromethane). While stirring at room temperature triethylamine (1.7 mL, 12.2 mmol) was added followed by chloroacetylchloride (0.63 mL, 7.9 mmol). The reaction stirred overnight. The next day the reaction was diluted with water and extracted using chloroform. The aqueous layer was washed with chloroform twice more. The combined organic material was washed with brine, dried with Na2S04, filtered, and concentrated. It was then used without any further purification. (1.39 grams collected). Calculated mass for C10H9CIN2O3, 240.03, observed mass, 241.0 (M+l, CI).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MUSC FOUNDATION FOR RESEARCH DEVELOPMENT; U.S. DEPARTMENT OF VETERANS AFFAIRS; LINDSEY, Christopher, C.; BEESON, Craig, C.; SCHNELLMANN, Rick, G.; (51 pag.)WO2018/85491; (2018); A1;,
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Related Products of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

B. 5-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l-one. Bis (pinacolato)diboron (815 mg, 3.21 mmol), dichloro[ 1 , 1 ‘-bis(diphenylphosphino) ferrocene]palladium (II) dichloromethane (240 mg, 0.29 mmol) and potassium acetate (860 mg, 8.76 mmol) were successively added to a solution of 5-bromoisoindolin-l-one (620 mg, 2.92 mmol) in methylene chloride (15 mL), followed by DMSO (5 mL). ). The resulting reaction mixture was heated at 100 C for 4h. Upon cooling, the crude mixture was diluted with water, extracted with methylene chloride (3x); the combined organic fractions were washed with water, brine, dried over magnesium sulfate, filtered, and the volatiles were removed under reduced pressure. The crude product was taken into hexanes, sonicated, and the precipitate was collected by filtration to afford the desired product (250 mg, 33%). MS (ESI) m/z 260.3 [M+ 1]+.

The chemical industry reduces the impact on the environment during synthesis 5-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
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Application of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

Statistics shows that 2-Oxoindoline-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 102359-00-2.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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Reference of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of isatin (1b) (0.3 gm, 1.53 mmol), andproline (2) (0.176 gm, 1.53 mmol) was heated in CH3CN at 80 C. After completion of startingmaterial, reaction mixture was cooled. The solvent was evaporated and the reaction mixture waspurified by silica gel column chromatography using hexane: ethyl acetate (8:2) to provideproduct (5b) as light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tiwari, Keshri Nath; Pandurang, Taur Prakash; Pant, Suyash; Sreelekha; Synthetic Communications; vol. 48; 7; (2018); p. 802 – 808;,
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Related Products of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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 mixed solution of compound 2b (5 g, 22 mmol), bisboronic acid pinacol (8.5 g, 33 mmol) and KOAc (3.2g, 33 mmol) in 1,4 dioxane (50 ml) was added Pd(dppf)2Cl2 (1g), and flushed with nitrogen. The reaction flask wassealed and the reaction was stirred overnight at 85C. After cooling to room temperature, an aqueous Na2CO3 solution(2.5M, 10ml), Pd(dppf)2Cl2 (1g) and 2,5-dibromo-3-nitropyridine (9 g, 33 mmol) were added. After flushed with nitrogenfor 10 minutes, the reaction flask was sealed and the mixture was stirred overnight at 85C. The reaction was pouredinto water and extracted with ethyl acetate. The organic phase mixture was dried over Na2SO4, dried by suction andpurified by silica gel column chromatography (PE:EA=10:1 to 1:1) to provide compound 2c as a yellow solid.HNMR(DMSO),9.1(s,1H),8.8(s,1H),7.7-7.8(m,3H),4.5(s,2H),3.1(s,3H).MS(ESI)m/z:347.9(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 6-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; NINGBO WENDA PHARMA TECHNOLOGY LTD.; WANG, Nenghui; (65 pag.)EP3406612; (2018); A1;,
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These common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)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. Formula: C21H21N3O5

2641 g of 2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (V) are suspended in 22 l of toluene and, at 19 C., 1300 g of N,N-carbonyl-diimidazole are added. The reaction mixture is subsequently heated under reflux for one hour and then, at 60 C., 4.5 l of ethanol are added. After cooling to 25 to 30 C., the precipitated reaction product is filtered off with suction, washed with ethanol and then dried. Yield: 2756 g; equivalent to 97.9% of theory. Melting point: 220.5 C.

The synthetic route of (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer HealthCare AG; US2005/182055; (2005); A1;,
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110568-64-4, name is 6-Nitroisoindolin-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: 6-Nitroisoindolin-1-one

A mixture of 5-nitro-1 lead noise isobutyl ketone Jie (100mg, 0.56mmoL), reduced iron powder (314mg, 5.6mmoL) was added to ethanol (2. OmL) and concentrated hydrochloric acid (0.5mL) and heated under reflux for 2 hours , TLC the reaction was complete. Cooling, the methanol solution saturated with ammonia (NH3) neutralizing the acid, diatomaceous earth filtration, washed with methanol, the solvent evaporated under reduced pressure to give a white solid 70.0mg, 84percent yield

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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Related Products of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

Salt (n-Bu4N)2[2-B10H9SH] (0.50g, 0.79mmol), N-(bromomethyl)phthalimide (0.38g, 1.68mmol), and cesium carbonate (0.26g, 0.39mmol) were placed in a 25-ml round-bottom flask and dissolved in 4ml DMF. The solution was heated to 80C in an argon atmosphere for 4h. After cooling to room temperature, a precipitate was removed by filtration and the solvent was distilled off on a rotary evaporator, and the dry residue was resuspended in 15ml of distilled water and allowed to stand in an ultrasonic bath to form a flocculated suspension. The precipitate was filtered off and washed with distilled water (2×10 ml) and ethyl acetate (3×5ml). Yield: 82%. Anal. calc. for C34H57B10N3O4S (%): C, 57.35; H, 8.07; N, 5.90; S, 4.50. Found (%): C, 57.15; H, 8.12; N, 5.81; S, 4.32. (0023) 1H NMR (CD3CN, delta, ppm): 7.79 (m, 8H, Ph), 5.04 (d, 2H, J=13.42, SCHaHb), 4.92 (d, 2H, J=13.42, SCHaHb), 3.09 (m, 8H, n-Bu4N+), 1.61 (m, 8H, n-Bu4N+), 1.34 (m, 8H, n-Bu4N+), 0.96 (t, 12H, n-Bu4N+), 0.60-2.10 (m, 9H, B10H9). (0024) 13C NMR (CD3CN, delta, ppm): 167.6 (CO), 135.8, 132.6, 124.4 (Ph), 59.3 (n-Bu4N+), 49.6 (SCH2), 24.3 (n-Bu4N+), 20.3 (n-Bu4N+), 13.8 (n-Bu4N+). (0025) 11B-{1H} NMR (CD3CN, delta, ppm): 3.5 (d, 1B), -4.4 (d, 1B), -18.2 (s, 1B), -26.5 (d, 5B), -30.1 (d, 2B). (0026) IR (CCl4): 3466,5 3091, 3062, 3027, 2959, 2933,2871, 2520, 2477, 1770, 1711, 1613, 1468, 1423, 1388, 1362, 1320, 1186, 1100, 1087, 1026, 978, 931, 860, 796, 717, 661, 603, 527cm-1.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kubasov; Turishev; Golubev; Bykov, A.Yu.; Zhizhin, K.Yu.; Kuznetsov; Inorganica Chimica Acta; vol. 507; (2020);,
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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.

Step A: Preparation of 5-BromoisoindoIine.To a solution of 5-bromoisoindoline-l,3-dione (8.117 g, 35.9 mmol) in THF (10 mL) was added boron trifluoride (8.40 mL, 108 mmol) dropwise. The reaction mixture was heated to reflux. After refluxing temperature was reached, borane tetrahydrofuran complex (144 mL, 144 mmol) was added dropwise and the reaction was stirred at reflux for 16 h. The mixture was cooled to 0 0C, cautiously treated with 3 N HCl (10 mL), and stirred at room temperature for 1 h. The aqueous mixture was washed with EtOAc, and the organic phase was discarded. The aqueous layer was basifed (pH 9-10) and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (4.02 g). LCMS m/z = 198.0 [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 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
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Electric Literature of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Example 271: (S)- l-Oxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)- pyridin-2-yl)methyl)isoindoline-5-carboxamide.Step 1. Methyl l-oxoisoindoline-5-carboxylate.To a 25 mL round bottom flask containing 5-bromo-2,3-dihydro-isoindol- 1-one (500 mg, 2.36 mmol), was added TEA. The resulting mixture was then stirred at 23 C for 2 min. At this time, MeOH (954 mu,, 23.58 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (54.6 mg, 0.094 mmol)(Xantphos) and palladium(II) acetate (10.59 mg, 0.047 mmol) were added to the flask. The reaction mixture was then flushed with argon and then with carbon monoxide. The flask was fitted with a rubber septa and a balloon of carbon monoxide was inserted through septa. The flask was stirred at 70 C overnight under carbon monoxide, allowed to cool, diluted with EtOAc (50 mL) and filtered through Celite eluting with EtOAc (300 mL). The solid remaining on the Celite pad was washed with DCM (200 mL) and DCM/MeOH (10: 1)(150 mL) and the filtrates concentrated to give a pale green solid (800 mg). A portion of this material was taken on to the next reaction with no further purification.

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; AMGEN INC.; BISWAS, Kaustav; BROWN, James; CHEN, Jian, J.; GORE, Vijay, Keshav; HARRIED, Scott; HORNE, Daniel, B.; KALLER, Matthew, R.; LIU, Qingyian; MA, Vu, Van; MONENSCHEIN, Holger; NGUYEN, Thomas, T.; YUAN, Chester, Chenguang; ZHONG, Wenge; ST. JEAN, David, J., Jr.; WO2012/177893; (2012); A2;,
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