Tag: M.W=200-300

Electric Literature of 20870-90-0,Some common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-2-oxoindoline, its application will become more common.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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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. 4702-13-0, name is N-Phthaloylglycine belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: N-Phthaloylglycine

Dissolve 2 g (9.75 mM) of N-phthaloylglycine in 20 mL of thionyl chloride, and reflux for 3 hours. At the end of that time, the thionyl chloride is evaporated under reduced pressure with the rotary evaporator. The product obtained is taken up three times in 50 mL of toluene, and subjected each time to evaporation under reduced pressure. At the end of the third evaporation, the product obtained is kept under vacuum for 30 minutes, then is taken up again in 20 mL of dry dichloroethane and stored as such until use.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universite De Nantes; Universite de Bourgogne; Institut National de la Sante et de la Recherche Medicale (INSERM); Robert, Jean-Michel; Troy-Fioramonti, Stephanie; Demizieux, Laurent; DeGrace, Pascal; US2018/265498; (2018); A1;,
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Electric Literature of 87-48-9, 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. 87-48-9, name is 5-Bromoindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred mixture of isatins 3a-c (3.4 mmol), potassium carbonate(0.94 g, 6.8 mmol) and catalytic amount of potassium iodidein dry DMF (10 mL), the appropriate alkyl halide 5a-d (3.7 mmol) or benzyl bromide 5e (0.63 g, 3.7 mmol) was added, and the mixture was heated under reflux for 3 h. Then, the reaction mixture was poured into ice-water, the obtained solid was collected, washed several times with water, and recrystallized from ethyl alcohol to afford the N-substituted isatin derivatives 6a-o [27].

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

Reference:
Article; Abo-Ashour, Mahmoud F.; Eldehna, Wagdy M.; Nocentini, Alessio; Bonardi, Alessandro; Bua, Silvia; Ibrahim, Hany S.; Elaasser, Mahmoud M.; Kry?tof, Vladimir; Jorda, Radek; Gratteri, Paola; Abou-Seri, Sahar M.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 184; (2019);,
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Application of 65435-04-3, A common heterocyclic compound, 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, molecular formula is C10H8ClNO2, 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 13 (FROM TABLE 3) 3-[4-(2-Carboxy-ethyl)-3-methyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid 2-Oxindole (6.7 g) was added to a stirred suspension of 23 g aluminum chloride in 30 mL dichloroethane in an ice bath. Chloroacetyl chloride (11.3 g) was slowly added and hydrogen chloride gas was evolved. After ten minutes of stirring, the reaction was warmed to 40..50 C. for 1.5 hours. Thin layer chromatography (ethyl acetate, silica gel) showed no remaining starting material. The mixture was cooled to room temperature and poured into ice water. The precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98%) of 5-chloroacetyl-2-oxindole as an off-white solid.

The synthetic route of 65435-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 5332-26-3

Preparation 5Preparation of 3-({r(1 ,1-dimethylethyl)oxy1carbonyl}amino)-2- (phenylmethyl)propanoic acida) diethyl 2-[(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)methyl]-2- (phenylmethyl)butanedioateTo a suspension of NaH (2.2 g, 54 mmole) in THF (200 ml.) was added diethyl 2-(phenylmethyl)butanedioate (12.5 g, 49.9 mmole). After 30 min at RT, bromomethyl phthalimide was added to the reaction mixture and the contents were stirred for 14 h at RT. The reaction was quenched with H2O (15 ml_), diluted with Et2O (300 ml.) and layers separated. The organic layer was concentrated under vacuum and the resulting residue recrystallized from EtOH (0) to give the title compound (13 g, 64%) as a white solid: LCMS (ES) m/z 410 (M+H)+.

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; SMITHKLINE BEECHAM CORPORATION; WO2008/121786; (2008); A1;,
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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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Safety of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione

Step 2 A solution of 2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (3.10 g, 12.6 mmol) in CH2Cl2 (25.0 mL) was added to a slurry of PCC (4.10 g, 19.0 mmol) in CH2Cl2 (15.0 mL) and stirred at room temperature for 3.5 hours. The reaction was diluted with Et2O (60.0 mL), decanted and the residue swirled with Et2O (2*40.0 mL). The combined ether layers were filtered through florisil and concentrated in vacuo to dryness, and the residue was recrystallized from ethyl acetate/hexane to give 2.01 g (65%) of 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione as colorless needles: mp 140.3-142.1 C.; 1H NMR (400 MHz, CDCl3) delta7.84, 7.74, 4.64, 2.72, 2.54, 2.09; 13C NMR (100 MHz, CDCl3) delta208.9, 168.1, 134.1, 131.9, 123.3, 48.4, 39.9, 28.6; IR (mull) 3062, 3031, 2958, 2949, 2919, 2885, 1775, 1762, 1721, 1708, 1611, 1465, 1436, 1419, 1393, 1379, 719 cm-1; HRMS (FAB) calcd for C14H14NO3: 244.0974, found 244.0976; Anal. Calcd for C-14H14NO3: C, 69.12; H, 5.39; N, 5.76. Found: C, 68.87; H, 5.47; N, 5.73.

The synthetic route of 104618-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fu, Jian-Min; US2003/100596; (2003); 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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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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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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