Category: indolines-derivatives

Electric Literature of 6941-75-9, 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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromoisoindoline- 1, 3-dione (3) (25 g, 110.6 mmol, 1.0 equiv) in THF (60 mL) was added BF3 (30 g, 442.4 mmol, 4.0 equiv) dropwise at 0 C. The mixture was stirred at 0 C for 1.5 h and BH3 (650 ml, 1.0 M, 6.0 equiv) was added dropwise at 0 C. Then the mixture was heated to 80C for 20 h and quenched by addition of methanol (100 mL) dropwise for 1 h at 0C. The mixture was concentrated to give a crude product of 5-bromoisoindoline (4) (22 g), which was used for next step directly.

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

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; QI, Xiangbing; LOU, Mingliang; WU, Enlong; CHEN, Peihao; WU, Qingcui; (41 pag.)WO2018/95260; (2018); A1;,
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Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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 6-chloroindolin-2-one (100 mg, 0.60 mmol), 3-(3,3,4,4- tetramethylborolan-l-yl)pyridine (184 mg, 0.90 mmol), Pd2dba3 (5.4 mg, 0.0060 mmol) and powdered K3PO4 (252 mg, 1.2 mmol) in w-BuOH (2 mL) was degassed by evacuation and refilling with Ar. Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2- yl)phosphine (11.4 mg, 0.024 mmol) was added under the atmosphere of Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 100 0C for 99 min. Later the reaction was cooled to rt and treated with degassed H2O (0.25 mL). The mixture was reheated under microwave irradiation at 110 0C for 1 h. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (0 to 6 %) in DCM as the eluent to provide the title compound as a pale yellow solid (100 mg, 80 %). %). 1H NMR (400 MHz, CD3OD) delta ppm 8.77 (d, J=I.52 Hz, 1 H), 8.52 (dd, J=4.80, 1.52 Hz, 1 H), 8.05 – 8.10 (m, 1 H), 7.52 (dd, J=7.33, 4.80 Hz, 1 H), 7.39 (d, J= 7.6 Hz, 1 H), 7.30 (dd, J=7.71, 1.39 Hz, 1 H), 7.17 (s,l H), 3.59 (s, 2 H); MS ESI 211.0 (100) [M + H]+, calcd for [C13H10N2O + H]+ 211.2.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
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Electric Literature of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-(4-bromobutyl)isoindoline-l,3-dione (3.33 g, 11.8 mmol), tert- butyl piperazine-l-carboxylate (2.2 g, 11.8 mmol) and Et3N (4.9 ml, 35.4 mmol) in CH3CN (50 mL) is heated at reflux for 16 h. The mixture is cooled and the solvent is evaporated. The residue is partitioned between EtOAc (70 mL) and water (70 mL). The organic layer is washed with brine (40 mL), dried (Na2S04) and evaporated. The residue is purified by flash column with 1:1 Hexane/EtOAc gives colorless oil (3.91 g, 85%).’HNMR (CDCI3,) delta: 7.83 (dd, 2H), 7,71 (dd, 2H), 3.71 (t, 2H), 3.41 (t, 4H), 2.34- 2.38 (m, 6H), 1.67-1.70 (m, 2H), 1.50-1.56 (m, 2H), 1.45 (s, 9H).LC-MS M+1: 388.12;

The chemical industry reduces the impact on the environment during synthesis 2-(4-Bromobutyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; HAN, Bingsong; KUNTZ, Judith D.; LIN, Jian; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; WO2012/154194; (2012); A1;,
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Synthetic Route of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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: Procedure C: A solution of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (1, 0.4 g, 3.0 mmol), 5-bromo-2-(4-methoxybenzyl) isoindolin-1-one (2, 1.0 g, 4.5 mmol) and potassium phosphate (1.91 g, 9.0 mmol) in 1, 4-dioxane (15 ml) was degassed with nitrogen for 10 min. Copper (I) iodide (0.28 g, 1.5 mmol) and trans-1, 2-diaminocyclohexane (0.17 g, 1.5 mmol) were added and the reaction was refluxed at 90 C. for 16 h. Progress of the reaction was monitored by TLC. After completion, solvent was removed under reduced pressure. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 2-(4-methoxybenzyl)-5-(4-methyl-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.55 g, 47%;

The synthetic route of 552330-86-6 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.; (55 pag.)US2017/121339; (2017); 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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Product Details of 7477-63-6

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25percent, 421 mg, 3.0 mmol) and H2O2 (30percent, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 °C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30percent NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89percent yield).

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
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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., Recommanded Product: 5-Bromoisoindoline-1,3-dione

Boc2O (2.58 g, 11.82 mmol) was added to a mixture of 5-bromoisoindoline-1,3-dione (2.23 g, 11.26 mmol) in THF (35 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?14% ethyl acetate/hexane) to give tert-butyl 5-bromoisoindoline-2-carboxylate (2.35 g, 7.88 mmol, 70.0%) as a white solid. 1H NMR (300 MHz, CDCl3):delta 1.51(9H,s), 4.58-4.68(4H,m), 7.07-7.17(1H,m), 7.35-7.44(2H,m).

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; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); A1;,
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These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-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. name: 5-(Trifluoromethoxy)indoline-2,3-dione

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-bromophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-bromophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5c): Melting point 255-257 C White solid, 97%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.98 (d, J = 3.96 Hz, 1H), 4.56-4.62 (m, 1H), 4.22-4.29 (m, 1H), 3.74 (d, J = 13.2 Hz, 1H), 3.63 (d, J = 16.82 Hz, 1H), 3.37 (d, J = 15.4 Hz, 1H), 2.90 (d, J = 13.96 Hz, 1H), 2.72-2.78 (m, 1H), 2.53 (d, J = 13.92 Hz, 1H), 6.53-6.62 (m, 2H), 6.88-7.55 (m, 21H, Ar); 13C-NMR(CDCl3, 100 MHz): delta/ppm 39.7, 47.3, 52.8, 53.2, 61.4, 67.2, 70.8, 100.8, 110.0, 121.9, 122.4, 122.5, 123.8, 124.3, 126.4, 126.5, 128.5, 128.6, 129.1, 129.2, 130.7, 131.5, 131.7, 131.9, 133.2, 136.2, 136.3, 138.1, 138.4, 138.6, 140.2, 144.6, 179.6, 197.1. EI-MS: m/z 869 (M+). Anal. Calcd for C44H34Br2F3N3O3: C, 60.77; H, 3.94; N, 4.83; Found: C, 60.89; H, 3.81; N, 4.75.

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

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);,
Indoline – Wikipedia,
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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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9Cl2NO

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., name: Potassium 1,3-dioxoisoindolin-2-ide

To a solution of 240 1-(bromomethyl)-4-methylbenzene (5 g, 27 mmol) in 28 DMF (30 mL) was added 242 potassium 1,3-dioxoisoindolin-2-ide (7.51 g, 40.5 mmol). The mixture was stirred at 100 C. for 14 hours. The reaction mixture was concentrated under reduced pressure to remove DMF. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=0 to 20%) to give 243 2-(4-methylbenzyl)isoindoline-1,3-dione (5.50 g, 81% yield). 1H NMR (chloroform-d 400 MHz) delta 7.85 (d, J=3.2 Hz, 2H), 7.84 (d, J=3.2 Hz, 2H), 7.34 (d, J=7.6 Hz, 2H), 7.13 (d, J=8.0 Hz, 2H), 4.82 (s, 2H), 2.32 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1074-82-4.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; (154 pag.)US2019/194189; (2019); A1;,
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Electric Literature of 64483-69-8,Some common heterocyclic compound, 64483-69-8, name is 5-Acetylindolin-2-one, molecular formula is C10H9NO2, 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 II 1,5-diacetyl-2-indolinone 48.9 g (0.279 mol) 5-acetyl-2-indolinone are stirred in 400 ml acetic anhydride in an oil bath at 140 C. for 2 h. The starting material dissolves during this time. Then the reaction mixture is left to cool, evaporated down, the precipitate is removed by suction filtering, washed with ether and the product is dried. Yield: 56.0 g (92.4% of theory) Rf=0.41 (silica gel, methylene chloride/methanol 50:1) C12H11NO3 (MW=217.223) Mass spectrum: m/z=216 (M-H)-

The synthetic route of 64483-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209302; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem