Category: indolines-derivatives

Synthetic Route of 603-62-3, 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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

The chemical industry reduces the impact on the environment during synthesis 3-Nitrophthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
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These common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, 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: 3-Methyloxindole

General procedure: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

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

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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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. name: 5-Bromoindoline-2,3-dione

General procedure: To a mixture of isatin (7a-e, 1.0 g) and hydrazine-hydrate (5 mL, ~30 mmol) in ethylene glycol,potassium hydroxide (10 equiv.) was added and the resulting reaction mixture was stirred at110-130 C for 2-3 h (monitored by TLC). The reaction mixture was cooled to roomtemperature, poured into ice-cold water (50 mL), acidified to pH 2 with 6N hydrochloric acidand extracted with ethyl acetate (3 x 30 mL). The organic extracts were combined, washed withbrine (15 mL), dried over sodium sulfate and concentrated in vacuo. The obtained residue waspurified by column chromatography using ethyl acetate-hexane as eluents to furnish 8a-e inmoderate yields.

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

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
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Related Products of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (R)-1-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-yl) amino)piperidin- 1-yl)prop-2-en-1-one (64.2) (100 mg, 0.3 mmol), tert-butyl 5-aminoisoindoline-2-carboxylate (1.5) (64 mg, 0.27 mmol), Cs2CO3 (177 mg, 0.54 mmol), tris(dibenzylideneacetone)dipalladium(0) (25 mg, 0.03 mmol), and Davephos (10 mg, 0.03 mmol) in tert-amyl alcohol (10 mL) was stirred at 100 C for 3 h. The mixture was quenched with the addition of water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to dryness to afford the crude product. The crude product was purified by column chromatography (hexanes/ethyl acetate: 1/1) to afford (R)-1-(3-((2-(isoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4- yl)amino)piperidin-1-yl)prop-2-en-1-one (I-65).The product was taken up in DCM/TFA (5 mL/3 mL) and stirred at room temperature for 30 min. The mixture was concentrated to dryness to afford the TFA salt of (R)-1-(3-((2- (isoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one (I-65) as a white solid (35 mg, 21%). [00915] LCMS: 433.1 [M+1]+. [00916] 1HNMR (400 MHz, CD3OD): delta 1.58-1.61 (m, 1H), 1.86-1.91 (m, 2H), 2.03-2.09 (m, 1H), 2.88-2.96 (m, 0.5H), 3.04-3.10 (m, 0.5H), 3.15-3.22 (m, 0.5H), 3.26-3.27 (m, 0.5H), 3.98- 4.10 (m, 1H), 4.29-4.39 (m, 1.5H), 4.49-4.63 (m, 4.5H), 5.47 (d, 0.5H), 5.84 (d, 0.5H), 6.05 (d, 0.5H), 6.28 (d, 0.5H), 6.40 (dd, 0.5H), 6.86 (dd, 0.5H), 7.36-7.39 (m, 1H), 7.58 (dd, 1H), 7.81 (s, 1H), 8.24 (d, 1H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 5-aminoisoindoline-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
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Related Products of 2307-00-8, The chemical industry reduces the impact on the environment during synthesis 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

A mixture of 1-phenylisatin (50 mg, 0.22 mmol) and 4-amino-N-methylpthalimide (40 mg, 0.22 mmol) was heated neat at 215 C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate and hexane as the eluent, giving the desired product as a yellow solid (8 mg, 0.02 mmol, 10%). 1H NMR (400 MHz): delta 7.88 (d, J=7.8, 1H), 7.83-7.80 (m, 1H), 7.51 (t, J=7.5, 1H), 7.47-7.18 (m, 6H), 7.02 (t, J=8.0, 1H), 6.91-6.79 (m, 2H), 6.58 (d, J=7.5, 1H), 3.22 (s, 3H); ESI-MS m/z found 382 (MH+).

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-Amino-2-methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Blackburn, Thomas P.; Bourtchouladze, Rusiko; Tallman, John F.; US2007/135509; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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. category: indolines-derivatives

Is added to the reactor 117.6 mg (0.65 mmol) 6 – chloro – isatin and 174.8 mg (0.78 mmol) 1, 3 – diphenyl – 1, 3 – c diketone, add 50 ml tetrahydrofuran and 5 ml DMF as the reaction solvent, adding 1 ml H2O2And 14.7 mg AlCl3As the catalyst, the electric jacket heated to 70 C, magnetic stirring reflux reaction for 12 hours. Thin-layer chromatographic trace to after the reaction is complete, evaporating the solvent under reduced pressure,, the resulting mixture by silica gel column chromatography separation and purification, drying to obtain the target compound 64.1 mg, total yield of 21.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6341-92-0, its application will become more common.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Tian Danni; Jia Minyi; Wang Xuechuan; Dong Hao; Wang Qiang; (12 pag.)CN108558895; (2018); A;,
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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

Example 7 : 2-({2-[2-(4-{(2S)-2-Hydroxy-3-[(methylethyl)amino]propoxy}phenoxy) acetylamino] ETHOXY} METHYL)-4-(2-CHLOROPHENYL)-5-CYANO-6-METLLYL-1, 4- dihydropyridine-3-carboxylate is synthesized according to Scheme VI. SCHEME VI 0 Ho- p OEt HO out C1 Ni C1 Me NC Me N N CHO CHO ci NC Me H 0 1. acetone, II. — . HO /O 2. II wEthyl 4- [2-FL, 3-DIOXOISOMDOLM-2-YDETHOXY1-3-OXOBUTANOATE. A solution of 2- (2- hydroxyethyl) isoindoline-1, 3-dione (10 g; 52.31 mmol) in DMF (150 ml) is cooled to 0C and treated with 1. 1 equivalents of a 60% dispersion of sodium hydride in mineral oil. After gas evolution has ceased, ethyl 4-chloro-3-oxobutanoate (7.75 g; 47.08 mmol) in 20 ml of DMF is added drop-wise, and the resulting solution is stirred overnight at room temperature. The pH of the mixture is then adjusted to 6-7 by the addition of 1 N HC1, and the product is partitioned between H2O and EtOAc. The aqueous phase is extracted again with EtOAc, and the combined organic phases are washed with water and brine, dried over magnesium sulfate, and concentrated to a crude residue, which is purified on a silica gel column, eluting with 25% EtOAc in hexane to obtain 7.52 g (23.54 mmol ; 50%) of the product as an oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3891-07-4.

Reference:
Patent; ARTESIAN THERAPEUTICS, INC.; WO2005/16885; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19155-24-9, These common heterocyclic compound, 19155-24-9, name is 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 mixture of 3,3-dimethyloxindole 41 (150 mg,0.93 mmol, 1.00 equiv) and Cs2CO3 (606 mg, 1.86 mmol, 2.00 equiv) in THF (4.70mL) was added o-nitrobenzyl bromide (302 mg, 1.40 mmol, 1.50 equiv). Thereaction mixture was stirred overnight. Then, the reaction mixture was extracted withEtOAc (3 x 6 mL) and washed with brine. The combined organic phases were driedover MgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?2-nitrobenzyl-3,3-dimethyloxindole 3a (258 mg, 93percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.16 (dd, J = 8.1, 1.4Hz, 1H), 7.51 (td, J = 7.6, 1.4 Hz, 1H), 7.44 (dddt, J = 8.1, 7.4, 1.4, 0.7 Hz, 1H), 7.28(ddd, J = 7.3, 1.3, 0.6 Hz, 1H), 7.17 (td, J = 7.7, 1.3 Hz, 1H), 7.12 (dq, J = 7.8, 1.0Hz, 1H), 7.09 (td, J = 7.5, 1.1 Hz, 1H), 6.61 (dt, J = 7.8, 0.8 Hz, 1H), 5.33 (d, J = 0.8Hz, 2H), 1.48 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 181.8, 148.2, 141.4, 135.8,134.2, 132.0, 128.5, 128.0, 127.6, 125.7, 123.2, 122.8, 108.8, 77.2, 44.5, 41.2, 24.8;IR (Neat Film NaCl) 2968, 1721, 1615, 1524, 1489, 1385, 1338, 1177, 1008, 858, 761cm-1; HRMS (MM: ESI-APCI+) m/z calc?d for C17H17N2O3 [M+H]+ : 297.1234;found: 297.1236.1 Vu, A. T.; Cohn, S. T.; Zhang, P.; Kim, C. Y. Mahaney, P. E.; Bray, J. A.; Johnston, G. H.; Koury, E.J.; Cosmi, S. A.; Deecher, D. C.; Smith, V. A.; Harrison, J. E.; Leventhal, L.; Whiteside, G. T.;Kennedy, J. D.; Trybulski, E. J. J. Med. Chem. 2010, 53, 2051?2062.NHOo-nitrobenzyl bromideCs2CO3THF, 23 °C(93percent yield)NOO2N4 3a

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
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Application of 603-62-3, 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. 603-62-3 name is 3-Nitrophthalimide, 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.

Step 1: To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J = 8 Hz, 1H, Ar), 7.92 (dd, J = 1, 8 Hz, 1H, Ar), 8.13 (dd, J = 1,8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; Celgene Corporation; MULLER, George, W.; SCHAFER, Peter, H.; MAN, Hon-Wah; ZHANG, Ling-Hua; GANDHI, Anita; CHOPRA, Rajesh; EP2683384; (2015); B1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, COA of Formula: C8H8N2O2

REFERENCE EXAMPLE 3 Preparation of N-(2,3-dihydro-1H-indole-5-yl)-methansulfonamide 5-nitroindoline (100 mg, 0.61 mmol) was dissolved in methanol (2 ml) and tetrahydrofuran (2 ml). Ammonium formate (192 mg, 3.05 mmol, 5 equivalent) and palladium/carbon (10%) in a catalytic amount were added at room temperature and refluxed at 40 C. for ten minutes. After completing the reaction, the reacting solution was filtrated through celite and concentrated under reduced pressure. Afterward, water (5 ml) was added to the residue, extracted consecutively 4 times with ethyl acetate (10 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure and then dried completely under a high-degree vacuum. The obtained compound, namely (2,3-dihydro-1H-indole-5-yl)-amine, was dissolved in dichloromethane (5 ml). Then, trimethylamine (0.063 ml, 0.45 mmol) was added to be cooled to -20 C. and mesyl chloride (0.035 ml, 0.45 mmol) was added to be stirred for 30 minutes at the same temperature. Water (5 ml) was added to separate dichloromethane solution, dried over anhydrous magnesium sulfate, purified through a flash column chromatography (an eluent: ethyl acetate/n-hexane=2/1, v/v) and then triturated with isooctane. As a result, the present compound (60 mg, productive yield 47%) was obtained as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta2.00 (s, 3H), 3.15 (t, J=8 Hz, 2H), 3.95 (t, J=8 Hz, 2H), 7.25 (d, J=8 Hz, 1H), 7.45-7.60 (m, 4H), 7.80 (s, 1H), 7.95 (d, J=8 Hz, 1H)

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

Reference:
Patent; CHEIL JEDANG Corporation; US2003/109568; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem