Category: indolines-derivatives

Synthetic Route of 954-81-4, 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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 3-1 (5.0 g, 17 mmol) was dissolved in dimethylformamide (DMF, 30 mL), and sodium azide (1.4 g, 1.3 eq.) was added. The reaction mixture was allowed to stir overnight, whereupon it was concentrated in vacuo to yield a white residue. The residue was dissolved in DCM, filtered through a silica gel plug, and solvent removed to afford N-[5- (azido)butyl]phthalimide (4.0 g, 91%) as a colorless thick oil. ?HNMR(300IVIHz, CDC13): = 1.30-1.44 (m, 2H), 1.50-1.75 (m, 4H), 3.21 (t, J= 7.5 Hz, 2H), 3.63 (t, J = 7.5 Hz, 2H), 7.60-7.70 (m, 2H), 7.75-7.80 (m, 2H). ?3C NIVIR(75 IVIFIz CDC13): = 23.8, 27.9, 28.2, 37.4, 51.0, 123.0, 131.9, 133.7, 168.2.

The chemical industry reduces the impact on the environment during synthesis N-(5-Bromopentyl)phthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LUMIPHORE, INC.; BUTLIN, Nathaniel G.; MAGDA, Darren; XU, Jide; (114 pag.)WO2016/106241; (2016); A1;,
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Related Products of 550-44-7, These common heterocyclic compound, 550-44-7, name is 2-Methylisoindoline-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.

Prepared according to a literature procedure (Beilstein I Org. Chem., 2012, 8, 192-200). N-Methylphthalimide (5 g, 30.4 mmol) was dissolved in MeOH (85 mL) andTHF (175 mL), then cooled to 0C. Sodium borohydride (1.15 g, 30 mmol) was added portionwise over 10 minutes, then the reaction mixture was stirred at 0C for a further 30 minutes. The reaction mixture was quenched with water and extracted with EtOAc, then the organic layers were dried over sodium sulphate and concentrated under reduced pressure, to afford the title compound (3.64 g, 73%) as a white solid.

The synthetic route of 550-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BROWN, Julien Alistair; CALMIANO, Mark Daniel; JONES, Elizabeth Pearl; KROEPLIEN, Boris; REUBERSON, James Thomas; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2015/86512; (2015); A1;,
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Application of 1336963-95-1, These common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-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.

2-Amino-4-bromo-3-fluorobenzoic acid To a solution of 6-bromo-7-fluoroindoline-2,3-dione (1.41 g, 5.80 mmol) in 2 N NaOH (15 mL), H2O2 solution (30%, 3 mL) was added at 0 oC and the resulting mixture was stirred at 0 oC for 30 min. After stirring at room temperature for 16 h, the mixture was poured into ice-water, and the solution was acidified with conc. HCl solution. The precipitate was collected by filtration and dried in the air to afford the desired product (1.2 g, 89% yield) as a white solid.

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; WU, Tao; REN, Pingda; LIU, Yi; LIU, Yuan; LONG, Yun, Oliver; WO2015/54572; (2015); A1;,
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Electric Literature of 181140-34-1, 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 181140-34-1 as follows.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
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Related Products of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
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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. 87-48-9, name is 5-Bromoindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H4BrNO2

General procedure: TiCl4 (0.7 mL, 6 mmol) wasadded to a stirred suspension of Zn powder (0.78 g, 12 mmol) infreshly distilled anhydrous THF (15 mL) at room temperature (r.t.)under a dry N2 atmosphere. After completion of the addition, themixture was refluxed for 2 h. The suspension of the low-valent titaniumreagent formed was cooled to r.t. A solution of isatin derivatives(2 mmol) in THF (10 mL)was added dropwise. The mixturewas stirred at room temperature for about 5 min under N2. Afterthis period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture wasquenched with 5% HCl (15 mL) and extracted with CH2Cl2(3 x 50 mL). The combined extracts were washed with water (350 mL) and dried over anhydrous Na2SO4. After evaporation of thesolvent under reduced pressure, the crude product was purified bycolumn chromatography (petroleum ether/EtOAc = 5:1) to give thepure products 9a-d.

The synthetic route of 87-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Delong, Wang; Lanying, Wang; Yongling, Wu; Shuang, Song; Juntao, Feng; Xing, Zhang; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 286 – 307;,
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Application of 675109-45-2, A common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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 1: methyl 3-((R)-l-((R)-2-(3,4-dimethoxyphenyl)-2-(3-oxoisoindolin-5- ylamino)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate; [00212] A solution of Intermediate 6 (300 mg, 2.0 mmol), 3,4- dimethoxyphenylboronic acid (370 mg, 2.0 mmol) and glyoxylic acid monohydrate (224 mg, 2.4 mmol) in acetonitrile/ DMF (4 mL, 4: 1) was heated in the microwave at 100 0C for 10 min. The reaction mixture was concentrated in vacuo and purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to yield IA (600 mg, 87%) as a yellow solid. MS (ESI) m/z 343.2 (M+H)+.

The synthetic route of 675109-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
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Electric Literature of 320734-35-8, A common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, 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.

To a cooled (-78C) solution of 7-bromooxindole (4.7g; 22.16 mmol) and N,N,N?, N?tetramethylethylenediamine (10.97 mL; 73.17 mmol) in dry THF (230 mL) was slowly added n-butyllithium solution (19.S mL; 48.76 mmol; 2.S M in hexane). The solution was stirred for 30 minutes at the same temperature and then, iodomethane (1.65 mL; 26.6 mmol) was added slowly. The reaction mixture was stirred at -20C for 1.5h, then,quenched with a saturated aqueous solution of NH4C1 and extracted with EtOAc.The organic layer was sried over MgSO4, filtered and concentrated in vacuo. The resultingcrude material was purified by silica gel chromatography (mobile phase: heptane/EtOAc)to afford, after solvent evaporation, 1.3 g (22%) of intermediate 217.

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); A1;,
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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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 356068-93-4

To a stirred solution of compound 1 (0.5 g, 1.67 mmol) in DMF (35 mL) at room temperature was added etaOBt (1.02 g, 7.52 mmol), triethylamine(2.12 mL, 15.03 mmol), ECDIetaC1(1.44 g, 1.52 mmol) and methyl 4-aminobutanate hydrochloride(0.77 g, 5.0 mmol) successively. The mixture was stirred for 24 h at room temperature and then was diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL) and the peta of solution was adjusted to 11-12 with 10 mol/L NaOH. The mixture was filtrated, the solid was collected, washed with water and dried to obtain crude yellow solid product 110-3 (0.32 g, 48.3%). LCMS: m/z 400(M+l), 1U NMR(DMSO-J6) deltal.77 (m, 2eta), 2.39 (m, 4H), 2.42 (s, 3H), 2.49 (s, 3H), 3.23 ( t, 2H), 6.85 (m, 2H), 7.60 (t, IH), 7.67 (s, IH), 7.71 (m, IH), 10.89 (s, IH), 13.68 (s, IH).

According to the analysis of related databases, 356068-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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Related Products of 7699-18-5, 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.

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

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; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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