Month: June 2021

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

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

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

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., category: indolines-derivatives

The conversion of substituted isatins to substituted Indazole-3- carboxylic acids is essentially the same methods as described by Snyder, H. R. et al. Thus, the substituted isatin (17-1) was suspended in IN NaOH and was heated at 50C for 30 min. The burgundy solution was allowed to cool to room temperature and was maintained for an additional one hour. The reaction mixture was cooled to 0 C and was treated with a solution of NaN02 (22 mmol) in water. This solution was added through a pipet submerged below the surface of H2S04 in water at 0c in 15 min. The reaction was maintained for an additional 30 min. A cold solution of Tin(II) chloride in con. HC1 was added to the reaction mixture over 10 min and the reaction mixture was stirred at the same temperature for an additional 2h. The solid filtered and washed with water several times and dried in vacuo to give quantitative mass balance of the product (17-2) with 80% NMR purity.

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; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, 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 446292-08-6, name: (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

100 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5- yl)methyl)isoindoline-l,3-dione of Formula (I), 1000 ml Methanol and 119 g methyl amine were added to RBF at 25C to 35C. The reaction was heated to 60C to 65C for 1-2 hours. To the reaction mass oxalic acid (15g) was added till to pH 5.5 to 6.0 and maintained for 30 minutes. The reaction mass was cooled to 45 to 50C andmaintained for 30 minutes. The reaction mass was cooled to 25 to 35C and maintained for 30 minutes. The product was filtered and washed with methanol (50 ml x 2) afforded the oxalate salt of (S)-4-(4-(5-(aminomethyl)-2-oxo-oxazolidin-3- yl)phenyl)morpholin-3-one of Formula (JO). ^

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DWIVEDI, Shriprakash, Dhar; PRASAD, Ashok; PAL, Daya, Ram; SHARMA, Mukul, Hari, Prasad; JAIN, Kuldeep, Natwarlal; PATEL, Naitik, Bharatbhai; WO2013/98833; (2013); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of isatin 1 (1 mmol) in THF (2 mL) was added La(OTf)3 (5 mol percent). The mixture was cooled to -78 °C and stirred at this temperature for 15 min. Then the solution of 2-(trimethylsilyloxy)furan 2 (1.5 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at -78 °C for 2 h. Later the mixture was brought to 20 °C and stirred for additional 0.5-1.5 h (Table 1). The reaction was monitored by TLC. After the completion of the reaction it was diluted with tetrahydrofuran (2.0 mL) and quenched with 10percent aqueous HCl (1.0 mL). The mixture was stirred for 0.25 h at room temperature, neutralized by the addition of a saturated aqueous NaHCO3 solution, and extracted with ethyl acetate (3.x.5 mL). The combined organic layer washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes). The inseparable diastereomers threo/erythro ratio of the product was determined by 1H NMR analysis of the crude reaction mixture.

The synthetic route of 7-Methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meshram, Harshadas Mitaram; Ramesh, Palakuri; Reddy, Bandi Chennakesava; Sridhar, Balasubramanian; Yadav, Jhillu Singh; Tetrahedron; vol. 67; 17; (2011); p. 3150 – 3155;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem