Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 61-70-1, SDS of cas: 61-70-1

No. A1-173: 1-(3-Bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (0127) (0128) Together, 1-methyl-1,3-dihydro-2H-indol-2-one (2.00 g, 14 mmol) and 1,2-dibromoethane (3.83 g, 20 mmol) were dissolved in abs. N,N-dimethylformamide (15 ml), sodium hydride (1.68 g, 42 mmol, 60% strength dispersion) was then added carefully a little at a time at a temperature of 10-15 C. and the mixture was stirred for another one and a half hours. Methanol and aqueous ammonium chloride solution were then added to the reaction mixture, and the aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2500 mg, 92% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.25 (m, 1H), 7.03 (m, 1H), 6.91 (d, 1H), 6.83 (d, 1H), 3.30 (s, 3H), 1.73 (m, 2H), 1.52 (m, 2H). 1?-Methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2.50 g, 13 mmol) was added to glacial acetic acid (23 ml), and fuming nitric acid (4 ml) was then added slowly and carefully. The resulting reaction mixture was stirred at room temperature for 30 minutes and then slowly diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium carbonate solution and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1800 mg, 57% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.25 (dd, 1H), 7.74 (d, 1H), 6.97 (d, 1H), 3.36 (s, 3H), 1.88 (m, 2H), 1.69 (m, 2H). In the next step, 1?-methyl-5-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1.80 g, 8 mmol) and tin(II) chloride dihydrate (7.45 g, 33 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1226 mg, 79% of theory) as a colorless solid. 1H-NMR (400 MHz, CDC138, ppm) 6.71 (d, 1H), 6.60 (dd, 1H), 6.25 (d, 1H), 3.52 (br. s, 2H, NH), 3.24 (t, 2H), 1.71 (m, 2H), 1.43 (m, 2H). In a round-bottom flask under argon, 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (130 mg, 1.0 equiv.) and (3-bromophenyl)methanesulfonyl chloride (261 mg, 1.4 equiv.) were dissolved together in abs. acetonitrile, pyridine (0.11 ml, 2.0 equiv.) and dimethyl sulfoxide (0.03 ml, 0.60 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1-(3-bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (235 mg, 81% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (m, 1H), 7.39 (m, 1H), 7.29 (m, 1H), 7.24 (m, 1H), 7.04 (m, 1H), 6.87 (d, 1H), 6.65 (d, 1H), 6.26 (s, 1H, NH), 4.13 (s, 2H), 3.30 (s, 3H), 1.78 (m, 2H), 1.54 (m, 2H). 13C-NMR (150 MHz, CDCl3 delta, ppm) 176.8, 141.7, 133.7, 132.6, 132.1, 130.8, 130.4, 129.5, 122.6, 120.8, 113.3, 108.3, 56.8, 27.4, 26.7, 19.7.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); A1;,
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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromoisatin

To a solution of 4-bromoisatin 30 (200 mg, 0.88 mmol) in THF/water (3:1, 3 mL) was added potassium 3-thienyltrifluoroborate (235 mg, 1.24 mmol) and K3PO4 (675 mg, 3.19 mmol) followed by Pd(PPh3)2Cl2 (62 mg, 0.09 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 ¡ãC. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL) and filtered through Celite?. The organic solution was washed with brine (10 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 30-40 ¡ãC petrol/acetone, 4:1) to afford the title compound (43) as an orange solid (120 mg, 59percent); mp 213-216 ¡ãC; numax (solid) 3098, 2927, 1727, 1584; deltaH (500 MHz, DMSO-d6) 6.85 (1H, dd, J = 7.9, 0.6 Hz, C(7)H), 7.20 (1H, dd, J = 7.9, 0.6 Hz, C(5)H), 7.50 (1H, dd, J = 4.9, 1.3 Hz, C(4′)H), 7.58 (1H, app t, J = 7.9 Hz, C(6)H), 7.62 (1H, dd, J = 4.9, 2.9 Hz, C(5′)H), 8.07 (1H, dd, J = 2.9, 1.3 Hz, C(2′)H), 11.13 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 110.8, 113.9, 123.8, 125.6, 126.3, 128.4, 135.8, 137.2, 138.0, 151.6, 158.9, 183.0; m/z (ESI-) 228 ([M-H]-, 100percent); HRMS (ESI-) C12H6N4O2S- ([M-H]-) requires 228.0125; found 228.0127.

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
Indoline – Wikipedia,
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Electric Literature of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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 tert-butyl 3-amino-4-methylphenylcarbamate (0.667 g, 3 mmol), 2-(l,3-dioxoisoindolin-2-yl)acetyl chloride (0.671 g, 3.00 mmol) in DCM (10 mL) was added diisopropylethylamine (1.048 mL, 6.00 mmol). After stirring 25 C for 15 h, saturated aqueous sodium chloride (25 mL) was added and extracted with ethyl acetate (3 x 25 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated. The crude product was purified by silica gel chromatography (100% ethyl acetate) to give the title compound as a white solid (1.15 g, 2.81 mmol, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta 9.70 (s, IH), 9.29 (s, IH), 7.91 – 7.99 (m, 2H), 7.83 – 7.91 (m, 2H), 7.56 (s, IH), 7.13 (d, J= 8.20 Hz, IH), 7.07 (d, J- 8.20 Hz, IH), 4.45 (s, 2H), 2.11 (s, 3H), 1.45 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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 the reaction vessel, 6-bromoisatin (10.0 g, 22 mmol) and 1N aqueous NaOH solution (48 mL) were added and the mixture was heated to 50C and stirred for 1 hour. The reaction solution was cooled to 0C, and a mixture of sodium nitrite (3.0 g, 22 mmol) and water (11 mL) was added slowly. Water (90 mL) and sulfuric acid (4.6 mL) were slowly added to the mixture at the same temperature and stirred. To the reaction mixture was added a mixture of tin chloride dihydrate (24.0 g, 53 mmol) and hydrochloric acid (40 mL) at 0 C, and the mixture was stirred at room temperature. The resulting solid was filtered, washed with water and dried to give the desired compound (8.53 g, 80% yield) as a yellow solid.

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; Korea Institute of Science and Technology; Sim Tae-bo; Noh Eun-ju; Yang Han-yong; (33 pag.)KR101936851; (2019); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 50727-04-3, A common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, molecular formula is C9H7NO3, 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-bromo-5-trifluoromethylpyridine (224 mg, 1 mmol), triethylene diamine (224 mg, 2 mmol),4-methoxyphthalimide (354 mg, 2 mmol), potassium phosphate (434 mg, 2 mmol),N, N-dimethylacetamide (2 ml) was added to the dry reaction tube and suspended in an oil bath at 120 C for 24 h.After cooling the reaction system, 15 ml of water was added and the aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined and the solvent was evaporated under reduced pressure to give 338 mg of a colorless solid, 5-methoxy-2- (2-(4- (5-trifluoromethylpyridyl) 2-piperazinyl) 1-ethyl) isoindole-1,3-dione in a yield of 78%.

The synthetic route of 50727-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yichun University; Zhu Qiming; Chen Mingwei; (20 pag.)CN106317021; (2017); A;,
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Synthetic Route of 110568-64-4, These common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-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.

Step 3: 5-aminoisoindolin-1-oneIron powder (2.51 g, 45 mmol), water (0.97 ml) and HCl (37percent, 0.74 ml), were added to a stirred suspension of the 5-nitroisoindolin-1-one (800 mg, 4.5 mmol) from step 2 of this example in EtOH (11.2 ml). The mixture was heated at 95 ¡ãC for 2h. Ammonia (7N in MeOH) was added (ImL) to make the pH of the mixture alkaline. The mixture was filtered to removed undissolved solids and the filter cake washed with EtOH (2×40 ml). The filtrate and organic washes were combined and concentrated in vacuum to give the titled compound.

Statistics shows that 6-Nitroisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 110568-64-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Formula: C9H7NO3

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ¡Á3 mL). The DCM layer was combined and washed with brine solution (25 ¡Á 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
Indoline – Wikipedia,
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Related Products of 20870-79-5, The chemical industry reduces the impact on the environment during synthesis 20870-79-5, name is 5-Nitroindolin-2-one, I believe this compound will play a more active role in future production and life.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

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-Nitroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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. Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
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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. 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H8N2O2

A mixture of 4-Bromo-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide (150 mg), Pd(OAc)2 (9.5 mg), BINAP (26 mg)5cesium carbonate (164 mg) and 5- Amino-2-methyl-isoindole-l,3-dione (148 mg) in 15 ml toluene was reflaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE: EtOAc (1:1). The toluene fraction was discarded and the solvent of the PE: EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE – THF). Yield 83 mg, 43 %.1H NMR (300 MHz, CDC13, rt) delta 0.13 (m, 2H5 CH2), 0.49 (m, 2H, CH2), 0.89 (m, IH, CH), 2.87 (t, broad, 2H, J= 7.2 Hz5 CH2), 3.18 (s, 3H5 CH3), 4.72 (t, broad, IH, NH), 6.75 (s, broad, IH, NH)5 6.98 (s, IH5 ArH)5 7.37 (dt, J= 8.1, J= 2.7, IH5 ArH)5 7.489 (d, IH5 J= 2.1, ArH)5 7.579 (d, IH5 J= 1.8, ArH)5 7.81 (d, IH5 J= 8.I5 ArH), and 8.14 (d, 2H, J= 8.7Hz5 ArH).MS: m/z 454.1 (M+)

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMOS CORPORATION; WO2008/75353; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem