Month: April 2021

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 324-03-8 as follows. Quality Control of 6-Fluoroindoline-2,3-dione

A solution of 6-fluoroindoline-2,3-dione (1 g, 6.06 mmol, SCRC) in anhydrous N,N-dimethylformamide (40 mL) was cooled to 00 C, whereupon NaH (60 % dispersion in mineral oil, 0.283 g, 7.09 mmol) was added in one portion and the reaction was stirred for 5minutes. lodomethane (0.443 mL, 7.09 mmol) was added and the reaction was stirred at 0 C for 30 minutes. The mixture was then poured into saturated aqueous NH4C1 and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (Mg504), filtered, and concentrated to give the crude product (1.2 g, 88 % purity), which was used without further purification.

According to the analysis of related databases, 324-03-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; HARDEE, David; BREWER, Jason; HASVOLD, Lisa; LIU, Dachun; MCDANIEL, Keith; SCHRIMPF, Michael; SHEPPARD, George; (139 pag.)WO2018/188047; (2018); A1;,
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These common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-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. Product Details of 17702-83-9

b) Preparation of 8-morpholinyloctylphthalimide 8-Bromooctylphthalimide (676 mg; 2.0 mmoles) and morpholine (0.35 ml; 4.0 mmoles) were dissolved in anhydrous acetonitrile (5 ml). Reaction times and process as per Example 1. 331 mg of pure product were obtained. Yield 48percent.

The synthetic route of 2-(8-Bromooctyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 20870-90-0, category: indolines-derivatives

EXAMPLE 28 Potassium tert-butoxide (1.66 g) was added portionwise to a stirred solution of (2S,4R)-4-hydroxy-4-(2-mercaptothien-4-yl)-2methyltetrahydropyran (3.15 g) in DMSO (25 ml) and the mixture was stirred at ambient temperature for 5 minutes. 5-Bromo-1-methylindolin2-one (3.71 g) and tetrakis(triphenylphosphine)palladium(O) (1.59 g) were added and the mixture was heated to 100 C. for 75 minutes. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and a mixture of ice and water. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p. 40-60 C.) and ethyl acetate as eluent. The material so obtained was further purified by column chromatography using a 5:1 mixture of methylene chloride and acetone as eluent. There was thus obtained (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thien-4-yl]tetrahydropyran (2.45 g, 48%), m.p. 125-127 C. (recrystallized from diethyl ether containing a few drops of methylene chloride) and m.p. 129.5-130.5 C. after a further recrystallisation from ethyl acetate; NMR Spectrum: 1.15 (d, 3H), 1.70 (m, 4H), 1.95 (m, 1H), 3.12 (s, 3H), 3.40 (s, 2H), 3.85 (m, 3H), 6.68 (d, 1H), 7.18 (m, 3H), 7.27 (d, 1H).

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-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US5478842; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 104618-31-7, 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 104618-31-7 as follows.

Preparation of 2-amino-6-phthalimido-4,5,6,7-tetrahydrobenzothiazole via 4-(phthalimido)-cyclohexanone; 1.0 Kg of 4-(phthalimido)-cyclohexanol was added in 20.0 L of acetone at 250C to 350C. The reaction mixture was cooled to 50C to 100C and treated with chromic acid solution. 0.2 L of isopropanol was added and stirred for 30 min. The reaction mixture was filtered and washed with acetone (1.0 L). The filtrate was treated with 0.4 kg sodium bicarbonate at 250C to 350C and stirred for 1 h. The reaction mass was again filtered, washed with acetone (1.0 L). Excess of acetone was distilled under vacuum. The residue was treated with 0.5 L ethanol followed by distillation of ethanol under vacuum. The reaction mass was cooled and treated with 3.36 L ethanol at 450C to 250C while gradual cooling. The reaction mixture was further cooled to 150C to 200C and treated with 0.22 L of bromine and 0.43 Kg of thiourea under stirring for 1 h. The reaction mixture was heated to reflux at 750C to 780C for 6 hrs. The reaction mixture was cooled and stirred for 1 hr at 50C to 100C. The product was isolated by centrifuge, washing with ethanol 0.66 L and drying under vacuum at 500C to 550C. (yield: 0.70 Kg).

According to the analysis of related databases, 104618-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2008/41240; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 16800-68-3, A common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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.

General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Ji-Quan; Li, Shu-Min; Wu, Chun-Feng; Wang, Xing-Lan; Wu, Ting-Ting; Du, Yao; Yang, Yuan-Yong; Fan, Ling-Ling; Dong, Yong-Xi; Wang, Jian-Ta; Tang, Lei; Catalysis Communications; vol. 138; (2020);,
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Application of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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.

5-Bromo-2-methylisoindolin-1-oneTo a solution of 5-bromoisoindolin-1-one (2500 mg, 11.79 mmol) in DMF (20 mL) under nitrogen, at 0 C, was added NaH (566 mg, 14.15 mmol) and the mixture was stirred for 30 min. After which, Mel (0.885 mL, 14.15 mmol) was added dropwise and the mixture was stirred at 0 C for 2 h. The reaction was quenched with sat. aqueous NH4CI, and extracted with EtOAc (3 x 30 mL). The organic layer was washed with brine, dried and concentrated to afford 5-bromo-2-methylisoindolin-1-one (2500 mg, 7.30 mmol, 61.9 % yield). LC-MS: m/z 226 (M+H)+1.02 min (ret. time).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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Indoline | C8H9N – PubChem

Application of 112656-95-8, 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. 112656-95-8, name is 7-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

The solution of 7-nitroisatin (15) (3 g, 0.016 mol), malonic acid (1.63 g, 0.016 mol) and piperidine (0.10 ml) in pyridine (10 ml) was refluxed for 20 hours. After cooling to room temperature, the solution of hydrochloric acid in 1,4-dioxane (16 %, 1 ml) was added. The solvent was evaporated in vacuum. The solid was washed with concentrated hydrochloric acid, the precipitate was collected by vacuum filtration, washed with small amount aqueous hydrochloric acid and water, dried on air to give 0.84 g (21 % yield) of (7-nitro-3-hydroxy-2-oxindole-3-yl)acetic acid. mp (exp.) = 242-243 0C. Spectrum NMR 1 (DMSO-d6, delta, ppm, J, Hz): 3.02 (d, J = 16.51, 1H), 3.12 (d, J = 16.51, 1H), 7.15 (dd, J = 7.09, J = 8.56, 1H); 7.75 (d, J = 6.97, 1H), 8.00 (dd, J = 1.10, J = 8.56, 1H), 11.06 (s, 1H). Spectrum NMR 13C (DMSO-d6, delta, ppm): 41,78; 71,41; 122,23; 124,39; 130,47; 131,10; 135,71; 140,04; 170,75; 178,94. IR spectrum (sm-1): 1470 (CH2), 1534; 1630 (NO2), 1698 (C=O), 1720 (C=O), 3227 (NH), 3447 (OH), 3000-3500 (OH). MS (EI, 70 eV), m/z (I, %): 252 (54, M+), 234 (46), 190 (85), 175 (76), 145 (100), 118 (46), 104 (32), 63 (26), 45 (55), 30 (55).

The chemical industry reduces the impact on the environment during synthesis 7-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zaryanova, Ekaterina V.; Lozinskaya, Nataly A.; Beznos, Olga V.; Volkova, Maria S.; Chesnokova, Nataly B.; Zefirov, Nikolay S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3787 – 3793;,
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Indoline | C8H9N – PubChem

Application of 141452-01-9, 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. 141452-01-9, name is Methyl indoline-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of Compound 113, 6-(pyridin-2-ylmethoxy)nicotinic acid[00135] LiOH (1 .345 M, 0.615 mL, 0.827 mmol) was added to a solution ofCompound 1 12 (0.101 g, 0.414 mmol) in THF (2 mL), followed by MeOH (0.6 mL) and the reaction mixture was stirred at rt for 26 h, concentrated to remove organic solvents, diluted with water, and washed with EtOAc (1 x). The aqueous phase was acidified to pH 2-3 with 2 M HCI, and the resulting precipitate was isolated by filtration, washed with water and dried to afford the title compound (79 mg, 83%) as a white solid.1H NMR (500 MHz, DMSO) 5 13.07 (s, 1 H), 8.71 (dd, J = 2.5, 0.8 Hz, 1 H), 8.56 (ddd, J = 5.0, 1 .8, 1 .1 Hz, 1 H), 8.19 (dd, J = 8.6, 2.4 Hz, 1 H), 7.81 (td, J = 7.7, 1 .7 Hz, 1 H), 7.46 (br d, J = 7.8 Hz, 1 H), 7.34 (ddd, J = 7.6, 4.8, 1 .1 Hz, 1 H), 7.04 (dd, J = 8.6, 0.8 Hz, 1 H), 5.50 (s, 2H). HRMS (ESI+): calcd for C12H11N2O3 (M + H)+, 231 .0764; found 231 .0760.

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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.

3 – (2 -chlorophenyl) propyne acid 4 – nitrophenyl-unitz (90.3 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 32 mg and gave rise 65% to unit_.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Acetylindolin-3-one, its application will become more common.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 6341-92-0 as follows. Quality Control of 6-Chloroisatin

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
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