Tag: M.W=200-300

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 2058-72-2 as follows. 2058-72-2

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
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Indoline | C8H9N – PubChem

118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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3335-98-6, 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. 3335-98-6 name is 1-Phenyloxindole, 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.

General procedure: A mixture of t-BuOK (1.63 g, 14.5 mmol) in EtOH (5.0 mL) was heated at 80 oC. Oxindole (10.0 mmol) was added, followed immediately by ethyl formate (1.09 mL, 13.5 mmol). Then, the reaction mixture was heated at 80 C for 5 min, and was cooled to 25 C. Crushed ice and H2O were added, then the mixture was acidified with 3 N HCl to pH = 3. The crude product was filtered and washed with water. Recrystallization from MeOH gave the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyloxindole, and friends who are interested can also refer to it.

Reference:
Article; Liu, Yin-Li; Xu, Xiu-Hua; Qing, Feng-Ling; Tetrahedron; vol. 74; 40; (2018); p. 5827 – 5832;,
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Indoline | C8H9N – PubChem

3335-98-6, A common compound: 3335-98-6, name is 1-Phenyloxindole, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

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, 1-Phenyloxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, 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 104618-32-8. 104618-32-8

A. 2-[4-(4-Benzyl-1-piperazinyl)cyclohexyl]-1H-isoindole-1,3(2H)-dione To a solution of 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)dione (3.78 g, 15.5 mmol), which was prepared according to the literature (J. Med. Chem., 1993, 1918), 1-benzylpiperazine (2.99 g/17.1 mmol) and AcOH (1.00 ml/17.1 mmol) in dichloroethane (50 ml) was added sodium triacetoxyborohydride (6.57 g/31.0 mmol) and the mixture was stirred for 2 days. The reaction mixture was poured into water (50 ml) and the mixture was extracted with dichloromethane (100 ml). The extract was washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel/dichloromethane) to give a colorless oil (5.00 g/89%). 1H NMR (CDCl13) delta 7.86-7.65 (m, 4H), 7.35-7.28 (m, 5H), 4.25-4.10 (m, 1H), 3.52 (s, 2H), 2.73-2.40 (m, 8H), 2.20-2.08 (m, 1H), 1.80-1.35 (m, 8H) ppm.

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 2-(4-Oxocyclohexyl)isoindoline-1,3-dione.

Reference:
Patent; Ikeda, Takafumi; Kawamura, Mitsuhiro; Murase, Noriaki; Nukui, Seiji; Shishido, Yuji; Kawai, Makato; Okumura, Yoshiyuki; US2001/46993; (2001); A1;,
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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., 99365-40-9

Pottasium tert-butoxide (0.085 g, 0.80 mmol) was added to a suspension of 6-bromoindolin-2-one (preparation 1, 3.00 g, 14.2 mmol) in dimethylsulphoxide (7 mL) and, after stirring for 10 minutes at ambient temperature, the mixture was heated to 40-45 C and methyl acrylate (4.00 mL, 44.40 mmol) was added dropwise over 70 minutes. After the addition, the mixture was stirred for 1 hour and then further potassium tert-butoxide (3.82 g, 34.00 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 1.5 hours. Water (45 mL) was added and heating was continued at 85 C for 4 hours and then the mixture was left to cool overnight. The resultant precipitate was filtered and the solid washed with water and hexanes to give the crude product. Recrystallization from ethyl alcohol gave the title compound (1.95 g, 42%) as a white solid. LRMS (m/z): 292/294 (M-1)-. 1H-NMR delta (DMSO-d6): 1.99-2.08 (m, 2H), 2.13-2.22 (m, 2H), 2.41-2.50 (m, 2H), 2.82-2.92 (m, 2H), 7.07 (d, J=3.0 Hz, 1H), 7.21 (dd, J=9.0/3.0 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 10.70 (br s, 1H).

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; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6326-79-0, Name is 6-Bromoisatin, 6326-79-0, 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.

Step 1: Preparation of 6-bromo-1H-indazole-3-carboxylic acid The solution of 6-bromoisatin (10 g, 22 mmol) in 1N aqueous NaOH solution (48 Ml) was stirred at 50 C. for 1 h. The mixture was cooled to 0 C. Sodium nitrite (3 g, 22 mmol) solution in water (11 Ml) was added dropwise for 15 min at 0 C. The mixture was added to the solution of water (90 Ml) and sulfuric acid (4.6 Ml) at 0 C. for 15 min. The mixture was added to the solution of conc. hydrochloric acid (40 Ml) and SnCl2.2H2O (24 g, 53 mmol). After 1 h, the mixture was filtered and washed with water. The solid was dried through air flow to give the titled compound (8.98 g). 1H NMR (300 MHz, DMSO-d6) delta 13.76 (bs, 1H), 7.87 (s, 1H), 7.55 (d, J=8 Hz, 1H), 7.27 (d, J=8 Hz, 1H), 2.44 (s, 3H).

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

Reference:
Patent; Sim, Tae Bo; Son, Jung Beom; Kim, Hwan; Park, Dong Sik; Choi, Hwan Geun; Ham, Young Jin; Hah, Jung Mi; Yoo, Kyung Ho; Oh, Chang Hyun; Lee, So Ha; Ha, Jae Du; Cho, Sung Yun; Kwon, Byoung Mog; Han, Dong Cho; US2012/130069; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 923590-95-8 name is 4-Bromoisoindoline hydrochloride, 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. 923590-95-8

Step e. TEA (126 ml, 903 mmol) was added drop-wise over 5 min to a stirred suspension of 4- bromoisoindoline HQ (100 g, 430 mmol) in THF (700 ml) and the mixture was cooled to 10C. The cooled mixture was then treated with a solution of di-tert-butyl dicarbonate (122 g, 559 mmol) in THF (300 ml) over 15 min whilst maintaining the temperature below 20C, and the resulting mixture was stirred at rt for 12 h. The reaction was concentrated under vacuum to give an oil, which was partitioned between EtOAc (600 ml) and water (600 ml). The aqueous phase was collected and extracted with EtOAc (2 chi 500 ml), and the combined organic extracts were washed with brine, dried over Na2S04, filtered and evaporated to dryness under vacuum to give the crude product as a solid (161 g). The crude solid was slurried in hexane (150 ml), filtered and the resulting solid washed with hexane (60 ml) before being dried under vacuum at rt to give the desired product as a solid (95.7 g, 75%). LCMS (Method R): rt 3.02 min, m/z 242 (-tBu)/198(-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) delta ppm 7.51-7.46 (dd, J = 7.8, 0.6 Hz, 1H), 7.38-730 (m, 1H), 7.29-7.21 (m, 1H), 4.73- 4.63 (d, 2H), 4.56-4.47 (d, 2H), 1.50-1.42 (d, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisoindoline hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: (2E,2’E)-3,3′-Benzene-1,4-diylbis(1-phenylprop-2-en-1-one) (1) (0.34 g, 1 mmol) was added in oneportion at room temperature to a stirred solution of isatinderivative 2 (1 mmol) and L-proline (3) (0.12 g, 1 mmol) inethanol (10 ml). The reaction mixture was stirred for 8 h.The solvent was then removed under reduced pressure, andthe residue was recrystallized from ethyl acetate as white powder.

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:
Article; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Keshipour, Sajjad; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 467 – 471; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 467 – 471,5;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

99365-40-9, Name is 6-Bromoindolin-2-one, 99365-40-9, 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.

To a warm, stirred solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL toluene and 60 mL ethanol was added tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.9 mmol) followed by 2M aqueous sodium carbonate (50 mL, 100 mmol) and thiophene-3-boronic acid (4.3 g, 33.6 mmol). The mixture was stirred at 100 C. in an oil bath for 12 hours. The reaction mixture was cooled, diluted with ethyl acetate (500 mL), washed with IN hydrochloric acid (200 mL), water (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give a black solid. The solid was triturated with methylene chloride to give 2.02 g (36%) of 6-thiophen-3-yl-1,3-dihydroindol-2-one as a purple-gray solid. 1H NMR (360 MHz, DMSO-d6) delta 10.49 (s, 1H, NH), 7.77 (s, 1H, Ar-H), 7.59 (m, 1H, Ar-H), 7.45 (m, 1H, Ar-H), 7.24 (m, 2H, Ar-H), 7.07 (m, 1H, Ar-H), 3.46 (s, 2H, CH2CO). MS m/z: 215 [M]+.

Statistics shows that 6-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 99365-40-9.

Reference:
Patent; Sugen, Inc.; US6689806; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem