Category: indolines-derivatives

Related Products of 2058-74-4,Some common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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 1 (3 mmol), 0.198 g malononitrile (3 mmol),0.420 g dimedone (3 mmol), and 0.025 g sodium acetate(0.3 mmol) were grinded with the pestle in mortar atambient temperature for 15 min. The resulting mixture wasair dried. Crude solid was then put on filter, rinsed withwater (2 9 2 cm3), and dried with water pump.

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

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Zaimovskaya, Tatiana A.; Egorov, Mikhail P.; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 755 – 760;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 7699-18-5 as follows. Computed Properties of C9H9NO2

General procedure: In 50 mL round flask, 4-(4-(hydrazinecarbonyl)-5-amino-1H-pyrazol-1-yl)benzenesulfonamide 15 (10 mmol, 0.3 g) was dissolvedin ethanol (20 mL) followed by the addition of the appropriate isatin derivative (10 mmol). Reflux was performed after the addition of a catalytic amount of acetic acid (0.5 mL) for 1 h. The formed precipitate, in case of 16a-e, was filtered, washed with hot ethanol and recrystallized from DMF / EtOH to give the targeted compounds 16a-e. Concerning compound 16f, the precipitate formed after cooling was filtered and recrystallized from DMF /EtOH. 4.1.7.4 4-(5-Amino-4-(2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-1H-pyrazol-1-yl)benzenesulfonamide (16d) Orange powder, 85% yield; mp > 300 C. IR (KBr) numax/cm-1 3414-3190 (NH2, NH), 1722-1690 (C=O), 1512 (C=N), 1322, 1156 (SO2). 1H NMR (DMSO-d6, 400 MHz) delta 3.80 (s, 3H, OCH3), 6.82 (d, 1H, J = 8.4 Hz, H-7 isatin), 6.96 (d, 2H, J = 10.2 Hz, Ar-H), 7.07 (s, 2H, NH2, D2O exchangeable), 7.49 (s, 2H, SO2NH2, D2O exchangeable), 7.83 (d, 2H, J = 8.4 Hz, Ar-H), 8.00 (d, 2H, J = 8.4 Hz, Ar-H), 8.61 (s, 1H, H-3 of pyrazole), 10.61, 11.07 (s, 1H, NH isatin, D2O exchangeable), 11.38, 13.02 (2s, 1H, NH hydrazone, D2O exchangeable). 13C NMR (DMSO-d6, 100 MHz) delta 56.41, 95.92, 111.50, 112.13, 116.20, 118.52, 121.22, 123.18, 123.97, 127.51, 137.77, 140.83, 142.96, 143.31, 152.46, 155.11, 155.83, 165.69, 166.47. MS m/z [%] 455 [M+, 9.06], 223 [100]. Anal. Calcd for C19H17N7O5S (455.45): C, 50.11; H, 3.76; N, 21.53; S, 7.04. Found: C, 50.27; H, 3.83; N, 21.75; S, 7.13.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ibrahim, Hany S.; Abou-Seri, Sahar M.; Tanc, Muhammet; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 583 – 593;,
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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C10H9NO2

The propyne acid 4 – nitrophenyl-unitz (57.3 mg 0.3 mmol), was used. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-like (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 0.3 mmol 45 mul -) and methylene chloride unitunitunito shown in the formula IV are placed in 3 ml a 25 ml unitunito-two-4h port bottle, reacted 30 C, and concentrated, under inert atmosphere protection, unitunitunitaceous conditions, and petroleum ether: petroleum ether: The ethyl acetate ratio 10:1 mixed solvent is eluted, eluent fractions, and the detected eluent fractions of all the products are collected, the solvent is evaporated and 25 mg the solvent is evaporated to obtain the unitz , which is a unitless 75%.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione, A new synthetic method of this compound is introduced below., name: 6-Methoxyindoline-2,3-dione

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products.

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; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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Indoline | C8H9N – PubChem

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. 74572-29-5, name is 5-Chloroisoindolin-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H6ClNO

[A] 2-(8-Amino-5,6,7,8-tetrahydro-isoquinolin-4-yl)-5-chloro-2,3-dihydro-isoindol-1-one In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (80.1 mg, 4.8 mmol), 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-ylamine (intermediate B-12 [A], 999 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150 C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2*125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.2 g, 80%) as a light yellow solid. MS: 314.2 (M+H+).

The synthetic route of 74572-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); A1;,
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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);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 114041-16-6, 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. 114041-16-6, name is 5,6-Dimethoxyisoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Compound 8 (70.6 mg, 0.24 mmol) and 5,6-dimethoxyisoindoline(68.5 mg, 0.38 mmol) were dissolved in CH3CN (30 mL), followed by addition of K2CO3 (138.8 mg, 1.00 mmol). The mixture was heated under reflux and stirred at 90 C for 6 h. After cooling and filtration, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate/triethyamine) = 10:10:1, v/v/v) to afford 13(56.8 mg, 59%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): d7.15-7.06 (m, 3H, Ar-H), 6.77 (s, 2H, Ar-H), 6.66 (dd, J = 3.1,0.5 Hz, 1H, Ar-H), 6.52 (d, J = 7.2 Hz, 1H, Ar-H), 4.84 (dt, J = 47.5,4.2 Hz, 2H, F-CH2), 4.37 (dt, J = 27.8, 4.3 Hz, 2H, O-CH2), 4.27 (t,J = 6.7 Hz, 2H, indole N-CH2), 3.87 (s, 10H, O-CH3, Ar-CH2-N), 2.65(t, J = 6.7 Hz, 2H, N-CH2), 2.08-2.05 (m, 2H, CH2). 13C NMR(100 MHz, CDCl3) d (ppm): 152.43, 148.63, 137.94, 131.86,127.08, 122.29, 119.61, 106.14, 103.84, 100.64, 98.63, 82.35(J = 169.2, F-CH2), 67.49 (J = 20.6, O-CH2), 59.32, 56.34, 52.75,44.12, 29.56. ESI-TOF MS calcd for C23H28FN2O3 [M+H]+:399.2084; found: 399.2076.

The synthetic route of 5,6-Dimethoxyisoindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Liang; Ye, Jiajun; He, Yingfang; Deuther-Conrad, Winnie; Zhang, Jinming; Zhang, Xiaojun; Cui, Mengchao; Steinbach, Joerg; Huang, Yiyun; Brust, Peter; Jia, Hongmei; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3792 – 3802;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Nitroindoline-2,3-dione

General procedure: A mixture of dimedone (0.140 g, 1 mmol), isatin (0.147 g, 1 mmol) and malononitrile (0.066 g, 1 mmol) was stirred in round bottom flask containing 5 mL of oxalic acid dihydrate:proline LTTM at room temperature for an appropriate time. After completion of the reaction, as indicated by TLC, 10 mL of water was added to the reaction mixture and the insoluble crude product was filtered off. The aqueous layer was evaporatedunder vacuumto recover the LTTM. The crude product was washed with distilled water(5 mL) and recrystallized from ethanol (10 mL).

According to the analysis of related databases, 611-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chandam, Dattatray R.; Mulik, Abhijeet G.; Patil, Dayanand R.; Deshmukh, Madhukar B.; Research on Chemical Intermediates; vol. 42; 2; (2016); p. 1411 – 1423;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem