Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-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 13220-46-7, category: indolines-derivatives

EXAMPLE 256 4-Methyl-3-[(4-piperidin-1-ylmethyl-phenylamino)-methylene]-1,3-dihydro-indol-2-one. The named compound is prepared by refluxing 0.045 gms E & Z-3-hydroxymethylene-4-methyl-1,3-dihydro-indol-2-one, prepared by substituting 4′-methyl-1,3 dihydro-indol-2-one for 1,3 dihydro-indol-2-one in the reaction of Example 1, with 0.064 gms. 4-piperidin-1-ylmethyl-phenylamine, prepared as in the reaction of Example 251, in tetrahydrofuran (1 mL) overnight. Following cooling to room temperature, solvent evaporation in vacuo, trituration with isopropanol and filtration the reaction yields the named compound as a solid in the amount of 0.0463 gms.

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; Andrews, Steven W.; Wurster, Julie A.; Wang, Edward H.; Malone, Thomas; US2003/199478; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 59-48-3, name is Indolin-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. SDS of cas: 59-48-3

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 mL of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid which had always present became very thick at this time. The solid was collected by vacuum filtration, washed with 100 mL of 50% acetic acid in water and then with 200 mL of water and sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

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

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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. 56341-37-8, name is 6-Chlorooxindole, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Chlorooxindole

To the mixture of 6-chloro-2-oxindole (4.4 g, 26 mmol) (Crescent) and 3-chloro-5-fluorobenzaldehyde (4.2 g, 26 mmol) (Aldrich) in methanol (200 mL) was added piperidine (2.3 g, 26 mmol) (Aldrich) dropwise. The mixture was then heated at 80 C. for 2 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-5-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 7.5 g, 92%).

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); 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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4N2O4

3-Nitrophthalimide (LOOGR) was taken into a hydrogenation vessel and dissolved using 500ML of dimethylformamide. Raney nickel catalyst (20gr, wet) was added to the solution and subjected to hydrogenation conditions initially at 20-30C UNDER 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogen uptake is over sample was drawn from the reaction mass and checked for the absence of 3-nitrophthalimide by TLC. The reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent was removed from the filtrate under reduced pressure at 60-80C. Water (500ML) was added to the residue and the mixture stirred for 20-30MIN. The product was isolated by filtration and dried at 60-70C to get a yellow crystalline solid of 3-aminophthalimide (80gr, 95%). Melting point: 262-4C.

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); A1;,
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 13220-46-7 as follows. Quality Control of 4-Methylindolin-2-one

Example 3 3-(3H-Isobenzofuran-1-ylidene)-4-methyl-1,3-dihydro-indol-2-one To a solution containing 4-methyloxindole (0.15 g, 1.02 mmol) and phthalide (0.178 g, 1.33 mmol) in 3.0 mL DMF was added 2.14 mL of sodium hexamethyldisilazane (1.0 M in tetrahydrofuran (THF)) over 1 min. The solution was stirred at room temperature for 30 min and then poured into 50 mL of 4% HCl to give a yellow solid. The aqueous mixture was extracted with EtOAc and the organic phase washed with saturated NaHCO3, H2O, dilute HCl, brine and the solution dried with Na2SO4. The solvent was removed in vacuo and the solid obtained was purified by chromatography (silica gel, CHCl3/EtOAc, 7:3). The solid obtained was recrystallized from EtOAc/hexanes to afford the title compounds (3.8 mg) as a yellow solid. 1H NMR (500 MHz, CDCl3) delta ppm 2.58 (s, 3H) 5.62 (s, 2H) 6.70 (d, J=7.81 Hz, 1H) 6.86 (d, J=7.32 Hz, 1H) 7.07 (t, J=7.57 Hz, 1H) 7.45 (m, 1H) 7.56 (m, 2H) 7.68 (s, 1H) 9.70 (d, J=6.83 Hz, 1H).

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US2004/19098; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 480-91-1, name is Isoindolin-1-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 480-91-1, category: indolines-derivatives

Example 7: Illustrative Preparation of 5-member Glutarimide Scheme 23: (1973) (1974) Step-1 To a stirred solution of 23-2 (448 mg, 3.37 mmol) and 23-1 (1000 mg, 3.37 mmol) and Potassium carbonate (931 mg, 6.74 mmol) in Acetone (20.0 mL ). It was stirred at room temperature for 16 hours. It was diluted with water and extracted with ethyl acetate. Organic part was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography using (silica, gradient, 0%-30% ethyl acetate in hexane to afford 3 as off white solid. Yield-20%; LC MS: ES+ 349.3.

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

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6872-06-6, name is 2-Methylindoline, 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 6872-06-6, name: 2-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6, 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. 22190-33-6 name is 5-Bromoindoline, 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.

1 , 1 -Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1 -carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at rt. After 10 min, the mixture gradually became a suspension. After 3 h, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and sucked under house vacuum for 5 h to give 1 , 1 -Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1 -carboxylate (ca 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) ppm 1 .50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H), 3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

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

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

PREPARATION 7 Preparation of ethyl 4-[2-(phthalimido)ethoxy]acetoacetate STR52 Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10 while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10 a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4572909; (1986); 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 32692-19-6 as follows. Recommanded Product: 32692-19-6

Example 33: 4-(5-Nitroindolin-1 -yl)phenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosideTo a mixture of 4-iodophenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside (18, 200 mg, 0.37 mmol), Cs2C03 (364 mg 1 .12 mmol) and 5-nitroindoline (91 .6 mg, 0.56 mmol) in a Schlenk tube under argon, x-Phos (9.1 mg, 0.019 mmol) and Pd2(dba)3 (3.85 mg, 0.0037 mmol), which had been pre-stirred for 15 min at 40C in dry toluene (3.5 mL), are added. The reaction mixture is degassed in an ultrasonic bath and stirred 140 h at 80C. The reaction mixture is diluted in EtOAc (50 mL) and washed with aqueous satd. NaHC03 solution (2 x 50-100 mL) and brine (50-100 mL). The aqueous layers are each extracted with EtOAc (2 x 50-100 mL) and the combined organic layers are dried over Na2S04, filtered and concentrated under reduced pressure. 20 (163 mg, 75%) is obtained as an orange solid after silica gel chromatography (5-40% gradient of EtOAc in petrol ether). [a]D20 +55 (c = 1 , CHCIs); 1H NMR (CDCI3): delta 2.02 (s, 3H, OAc), 2.04 (s, 6H, 20Ac), 2.18 (s, 3H, OAc), 2.20 (s, 3H, OAc), 3.19 (t, J = 8.6 Hz, 2H, CH2), 4.08 (m, 4H, CH2, H-6a, H- 5), 4.28 (dd, J = 5.2, 12.5 Hz, 1 H, H-6b), 5.38 (t, J = 10.1 Hz, 1 H, H-4), 5.44 (dd, J = 1.8, 3.5 Hz, 1 H, H-2), 5.50 (d, J = 1 .6 Hz, 1 H, H-1 ), 5.55 (dd, J = 3.5, 10.1 Hz, 1 H, H-3), 6.73 (d, J = 8.9 Hz, 1 H, C6H4, C6H3 ) 7.13 (m, 3H, C6H4, C6H3 ), 7.21 (m, 1 H, C6H4, C6H3), 7.95 (s, 1 H, C6H3, C6H4 ), 7.98 (dd, J = 2.3 Hz, 8.9 Hz, 1 H, C6H3, C6H4 ); 13C-NMR (CDCI3): delta 20.90, 20.92, 21 .09, 21 .65 (40Ac), 27.27 (CH2), 53.85 (CH2), 62.28 (C-6), 66.03 (C-4), 68.98 (C-3), 69.40 (C-2), 69.53 (C-5), 96.36 (C1 ), 105.52 (C6H4), 1 17.81 ,1 17.92 (C6H4, C6H3), 121 .32 (C6H3), 122.03 (C6H4), 126.27 (C6H3), 128.40 (C6H3), 137.21 (Car-N) , 169.90, 170.19, 170.23, 170.70 (C=0); ESI-MS calcd. for C28H31N20i2 [M+H]+: 587.19; found 587.29.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; HEROLD, Janno; WO2011/73112; (2011); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem