Indolines-derivatives

Related Products of 7699-18-5, A common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: 4.4.14 (Z)-3-((2-(3,5-difluorophenyl)-1H-benzo[d]imidazol-6-yl)methylene)-5-methoxyindolin-2-one (5n) Compound 5n was prepared according to the method described for compound 5a, employing aldehyde 11d (129 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81 mg, 0.5 mmol) to obtain the pure product 5n as a yellow solid (110 mg, 55%); mp: 296-298 C; IR (KBr): 3425, 3165, 2925, 2357, 1673, 1640, 1560, 1410, 1282, 1190, 1120, 942, 866, 745 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.69 (bs 1H), 8.04 (s, 1H), 7.91 (s, 3H), 7.75 (s, 1H), 7.62 (s, 2H), 7.47 (t, J = 7.9 Hz, 1H), 7.05-6.87 (m, 2H), 3.79 (s, 3H); 13C NMR (75 MHz, CDCl3 + DMSO-d6): delta 168.8, 164.4 and 161.3 (d, J = 246.1 Hz), 163.7 and 161.7 (d, J = 246.1 Hz) 160.7,154.6, 149.7, 141.2, 137.5, 134.6, 128.7 (d, J = 4.9 Hz), 127.6, 125.4, 124.8, 122.7, 120.6, 118.6, 109.8, 109.4, 105.7, 55.2; MS (ESI): m/z 404 [M + H]+; HRMS (ESI): calcd for C23H16O2N3F2 m/z 404.12308 [M + H]+; found 404.12758.

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:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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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. 111992-61-1, name is 2-(3-Bromo-2,2-dimethylpropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(3-Bromo-2,2-dimethylpropyl)isoindoline-1,3-dione

Step 3 A suspension of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.3 mmol, 1.00 equiv), 2-(3-bromo-2,2-dimethylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione (570 mg, 1.95 mmol, 1.50 equiv) and cesium carbonate (847 mg, 2.60 mmol, 2.00 equiv) in NMP (50 mL) was stirred at 100 C. for 12 h under nitrogen atmosphere. It was quenched with water (150 mL). The resulting solution was extracted with ethyl acetate (5*30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10/1). This resulted in 280 mg (41%) of 2-(2-[[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-2-methylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione as a yellow oil.

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; Principia Biopharma Inc.; Goldstein, David Michael; US8673925; (2014); B1;,
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Reference of 675109-45-2, 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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

6-Ammnoisoindolin-1-one (15.34 mg, 0.104 mmol) was dissolved in DCM (1.0 mL) along with pyridine (0.039 mL, 0.487 mmol) and DIEA (0.032 mL, 0.183 mmol). Intermediate 14SF (28 mg, 0.061 mmol) in 2 mL of DCM was added dropwise, and the reaction mixture was stirred at room temperature for 50 minutes. The reaction was quenched with 1.0 N HC1 (0.5 mL). All solvent was removed under vacuum. The crudewas dissolved in DMSO/THF (2:1, 6 mL) and purified via preparative LC/MS (method C,40-100% B over 18 mm, then a 5-mm hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to yield Example 178 (10.7 mg, 31% yield). ?H NMR (500MHz, DMSO-d6) 8.72 (s, 1H), 8.56 (s, 1H), 8.51 (br. s., 1H), 7.86 (d, J=10.7 Hz, 2H), 7.81 (br. s., 2H), 7.61 (br. s., 1H), 7.46 (d, J=5.8 Hz, 1H),5.48-5.38 (m, 1H), 4.54 (d, J12.2 Hz, 1H), 4.41 (dd, J=12. 1, 7.2 Hz, 1H), 4.29 (s, 2H),4.08 (s, 3H), 3.64 (dd, J15.9, 9.8 Hz, 1H), 3.36 (d, J=13.7 Hz, 1H), 2.62 (s, 3H);LC-MS: method C, 2 to 98% B. RT = 2.21 mm, MS (ESI) m/z: 572.30 (M+H).Analytical HPLC purity (method B): 100%.

The synthetic route of 6-Amino-2,3-dihydro-1H-isoindol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
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Synthetic Route of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 0.91 g (3.6 mmol) N-(2 -bromoethyl) phthalimide was dissolved 20 mL DMF, added 0.53 g (3 mmol)1-benzylpiperazine, 0.62 g (4.5 mmol) K2CO3, heated to 60-70 ¡ãC reacted for 4 h, TLC detection, until the benzylpiperazinewas complete reaction. 30 mL of water was added, extracted three times withethyl acetate (20 mL¡Á 3), the organic layer was extracted four times (30mL ¡Á 4)with saturated brine, dried with anhydrous magnesium sulfate, and the solventwas distilled off under reduced pressure, cooled to room temperature, silicagel column chromatography (100-200 mesh silica gel, eluent petroleum ether:ethyl acetate = 1:1 – 1: 4) to give 0.7 g (67percent yield) as a white solid. #10;

The synthetic route of 2-(8-Bromooctyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
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Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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: 3891-07-4

A solution of 126 (5 g, 26 mmol) in DMF (50 mL) was treated with sodium hydride (1.1 g, 32 mmol, 70 % dispersed in mineral oil) for 30 minutes at room temperature, followed by addition of BnBr (6.7 g, 39 mmol). After additional 1 hour, the reaction was quenched by water (200 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 10 % – 20 % ethyl acetate in petroleum ether to afford 127 as a white solid (4.8 g, 65 %).(ES, m/z) [M+H]+ 282.0; 1H NMR (300 MHz, CDC13) delta 7.85 – 7.88 (m, 2H), 7.71 – 7.74 (m, 2H), 7.25 – 7.31 (m, 5H), 4.55 (s, 2H), 3.95 (t, / = 6.0 Hz, 2H), 3.74 (t, / = 6.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3891-07-4, its application will become more common.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest J.; MU, Changwei; SELNICK, Harold G.; SHI, Feng; VOCADLO, David J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/62157; (2012); A1;,
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Electric Literature of 100510-65-4, These common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-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.

To a’ -solution of 110 mg di-imidazol-1-yl-methanone and 6mg imidazole- in 2. ml tetrahydrofuran a solution of- 100 mg .6-amino-3,3-dimethyl-l, 3-dih’ydro-indol-2-one in. 1. mltetrahydrofuran was slowly added at 0C. After stirringat 0C’. for ‘3’0 minutes and 1 hour at room temperature 103mg . ” . 2-methyl-2-[(quinolin-4-ylmethyl)-amino]-propionicacid methyl ester were added and the reaction mixture was ,allowed to warm up to room temperature.. After 16 hours.stirring at .room ‘temperature the solution was heated for1 -hour -“at 70C.: After cooling to room temperature thesolvent of the mixture was removed .under reduced pressureand the residue was purified by preparative HPLC (C18reverse phase’?? column, ‘ elution ? with a water/ acetonitrile gradient with CL .%’? “trifluoroacetic acid). Lyop.hiliza.tion of the’-solution’yielded -a. white -solid, that was purified, .in addition.’by. flash chromatography on silica gel with a ‘d’ichloro-methane/methanol’ . gradient. The . fractions containing ‘the product? were’ combined and evaporated to yield ? – a . . white . solid.?Yield: 7.5 mg ‘ ?,?…M+H+ measured = ‘429 ‘1H-NMR (500 MHz’, ? DMSO/TMS).: d .= 10.50 (s, 1H) ; 8.87 (d,?1H); 8.25 (d, 1H) ; 8.09-(d, 1H) ; 7.82 (t, 1H) ; 7.70 (t,1H); 7.63 (d, 1H) ; 7.42 (d, IE).; 7.07 (d, 1H) ; 7.01 (s,1H); 5.14 (s, 2H); 1.43 (s, 6H); 1.29 (s, 6H)

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10642; (2006); 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.

To the mixture of 6-chloro-2-oxindole (5.3 g, 32 mmol) (Crescent) and 3-chloro-4-fluorobenzaldehyde (5 g, 32 mmol) (Aldrich) in methanol (200 mL) was added piperidine (2.7 g, 32 mmol) (Aldrich) dropwise. The mixture was then heated at 50 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-4-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 8 g, 82%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chlorooxindole, its application will become more common.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
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Application of 2058-72-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2058-72-2 name is 5-Bromo-1-methylindoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A solution of carbonyl compounds 1 (0.30 mmol), isatins 2 (0.40 mmol) and 50 mol% Cat. Et2NH (0.15 mmol) in EtOH (2.0 mL) was stirred at 40 oC for 15 h. After completion of the reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc= 5:1~3:1) were carried out to furnish the corresponding products 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Lin, Bing; Lu, Yi; Huang, Jun-Fei; Gong, Yi; Liu, Huan-Huan; Liu, Xiong-Li; Tian, Min-Yi; Zhou, Ying; Yuan, Wei-Cheng; Synthetic Communications; vol. 47; 6; (2017); p. 609 – 617;,
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Related Products of 1127-59-9,Some common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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: Isatin (0.5 g, 3.34 mmol) was added into a stirred solution ofKOH (0.56 g, 10.02 mmol) in ethanol 10 ml at 80 C. The reactionmixture was stirred at 0 C for 24 h. The mixture was added to50 g ice water. The pH was adjusted by the solution of 2 N HCl to4?5. The mixture was cooled overnight and filtered. The residuewas recrystallized by the mixture of petroleum/ethyl acetate(5:1). Compound 4 (0.8 g) was obtained and the yield was 96.87percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Liao, Chen; Liu, Yan; Liu, Chunxia; Zhou, Jiaqi; Li, Huilan; Wang, Nasi; Li, Jieming; Liu, Taiyu; Ghaleb, Hesham; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 845 – 854;,
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Synthetic Route of 5428-09-1, These common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-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: Equimolar amounts of triethoxysilane and a respective aminated alkene were stirred with 330 ppm Cp2PtCl2 (i.e., 330 mumol per mol of silane) without solvent at 85 ¡ãC in a sealed schlenk tube under argon. After cooled to room temperature, the crude was purified by vacuum distillation or silica gel column chromatography to afford the desired product. The yield and the selectivity (i.e., the ratio of gamma-isomer/beta-isomer) were calculated on the basis of 1H NMR spectrum.

The synthetic route of 5428-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Huarui; Zheng, Chaoyue; Chen, Naiwu; Zhu, Jie; Gao, Deqing; Tetrahedron Letters; vol. 58; 16; (2017); p. 1576 – 1578;,
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