Indolines-derivatives

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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4403-36-5

To 3-exo-[(R)-1-((S)-2-methyl-propane-2-sulfinylamino)-2-(2,4,5-trifluoro-phenyl)-ethyl]-8- aza-bicyclo[3.2.1]octane (265 mg, 0.68 mmol) in dichloromethane/1M NaOH (1/1, 5 mL) is added 2-phthalimidoethane sulfonyl chloride (577 mg, 2.05 mmol) then the resulting mixture is stirred at 50C during 16h. It is extracted with dichloromethane, the organic phase is dried and evaporated to give a white solid. MS: 626 [M+H]+HPLC (Zorbax SB C18, 2min method (0-0.8min 10-95%ACN, 0.8-1.5min 95%ACN, 1.5- 1.6min 95-10%ACN, 1.6-2min 10%ACN): 1.25 min.

According to the analysis of related databases, 4403-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/115821; (2007); A2;,
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Application of 88150-75-8, The chemical industry reduces the impact on the environment during synthesis 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, I believe this compound will play a more active role in future production and life.

Orthochlorobenzaldehyde (67.5 g, 0.48 M) was reacted with ethyl 4[2-(phthalimido)ethoxy acetoacetate (100 g, 0.31 M) in the presence of pyridine acetic acid in benzene at 80/82 C. for 12 hrs and cooled to room temperature. To the reaction mass water was added. Organic layer was separated and benzene was distilled out and the residue was washed with hexane.

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, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Purohit, Arun Kumar; Desai, Brahmader Chilu; Shete, Balasaheb Dashrath; Bagwan, Salim Abbas; US2004/44218; (2004); A1;,
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Electric Literature of 59-48-3, 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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1 H-NMR (360 MHz, DMSO-d6) delta 10.75 (s, br, NH), 7.83 (d, J=8Hz, 1H), 7.78 (s, 1H, H-4) 6.88 (d, J=8Hz, 1H),.3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

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

Reference:
Patent; Sugen, Inc.; US6114371; (2000); A;,
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Related Products of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Intermediate No.18fer/-Butyl (5-bromo-l-oxo-l ,3-dihydro-2 /-isoindol-2-yl)acetate5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0 C. NaH (38 mg, 0.94 mmol, 60% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0 C for 15 minutes before tert-butyl bromoacetate (92 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0 C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added. The mixture was extracted with EtOAc, and the organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-20% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. LRMS (ESI) calc’d for C14H16BrN03 [M+Na]+: 348, Found: 348.

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); A1;,
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Synthetic Route of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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.

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 65 mg (42%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.30 (s, br, 1H, NH-1′), 12.05 (s, br, 1H, COOH), 10.67 (s, br, 1H, NH-1), 7.57 (s, 2H, H-vinyl, H-4), 7.12 (d, J=2.65 Hz, 1H, H-2′), 6.91 (d, J=7.82 Hz, 1H, H-6), 6.74 (d, J=7.82 Hz, 1H, H-7), 2.65 (t, J=6.94 Hz, 2H, CH2CH2COOH), 2.46 (t, J=6.94 Hz, 2H, CH2CH2COOH), 2.30 (s, 3H, CH3), 2.25 (s, 3H, CH3); MS m/z (relative intensity, %), 311 ([M+1]+, 100).

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Electric Literature of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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 10 ml schlenk bottle by adding 5 – bromo -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material 5 – bromo -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product 5 – […], I – 6, the isolation yield is 76%

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

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
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These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

To A NN-DIMETHYLFORMAMIDE/ACETONITRILE, (2 mL: 10 mL), mixture containing ethyldiisopropylamine (0.52 ML, 3 mmol) was added 2-oxoindoline-5-carboxylic acid (0.354 g, 2.0 mmol; described in: Sun L. et al. J. MED. Chem. 2000, 43 (14), 2655:), O- (BENZOTRIAZOL-1-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (0.77 g, 2.4 mmol) and 1-HYDROXYBENZOTRIAZOLE hydrate (0.324 g, 2.4 mmol) and stirred for 5 min at room temperature. Thereafter, 2- (AMINOMETHYL) pyridine (0.562 g, 5.2 mmol) was added and the resulting reaction mixture was stirred for 90 min followed by addition of a saturated aqueous NAHCO3 solution (10 ML). The solvents were removed in vacuo and 0.364 g (68% yield) of the title product was obtained as a white solid after purification on a silica gel column using chloroform/methanol, (9: 1), as the eluent : 1H NMR (DMSO-d6, 400 MHz) 8 10. 66 (s, 1 H), 8.96 (t, 7= 5. 6 HZ, 1 H), 8.55 (d, J = 4.4 Hz, 1 H), 7. 85 (d, J = 8. 0 HZ, I H), 7.83 (s, 1 H), 7. 78 (t, J = 7.6 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.29 (t, J= 6. 4 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 4.59 (d, J = 6.0 Hz, 2 H), 3. 58 (s, 2 H); MS (EI) MLZ 268 (M++1).

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
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Related Products of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
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39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of aromatic diamine derivatives (2 mmol) and a 1,2-dicarbonyl compound (2 mmol) in ionic liquid (2 mL) was stirred atroom temperature for the appropriate time. The progress of the reaction was monitored by TLC (n-Hexane: EtOAc, 7:3), after completion of the reaction, the reaction mixture was diluted with water and extracted using diethyl ether (30 ml). The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford the corresponding product. The residual ionic liquid was dried under vacuum and reused. The same procedure was repeated for the reaction of aromatic anilines with isatin and acenaphthoquinone and phenaacylbromide. All the products obtained were characetrised by IR,1HNMR, 13CNMR and Mass studies.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bhargava, Sangeeta; Soni; Rathore, Deepti; Journal of Molecular Structure; vol. 1198; (2019);,
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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 5332-26-3 as follows. Product Details of 5332-26-3

2-Ethylacrylic acid (250 mg, 2.5 mmol) was dissolved in anhydrous dimethylformamide (8.0 mL), to the solution were added N-bromomethylphthalimide (660.0 mg, 2.8 mmol) and potassium fluoride (291.0 mg, 5.0 mmol), and the mixture was stirred for 12 hr at 80 C. under nitrogen atmosphere. The reaction mixture was concentrated in vacuo, and the obtained residue was extracted with dichloromethane after the addition of water (80 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the objective substance (463.1 mg, 72%). 1H-NMR (CDCl3) delta: 7.94 (dd, J=5.4, 3.2 Hz, 2H), 7.79 (dd, J=2.8, 1.4 Hz, 2H), 6.16 (d, J=1.0 Hz, 1H), 5.80 (s, 2H), 5.57 (d, J=1.5 Hz, 1H), 2.35-2.25 (m, 2H), 1.06 (t, J=7.4 Hz, 3H).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2005/182032; (2005); A1;,
Indoline – Wikipedia,
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