Tag: M.W=100-200

Electric Literature of 13220-46-7, These common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-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.

4-Methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one A mixture of 4-methyl-2-oxindole (147 mg) (prepared as described in Compound IN-015), 3-methyl-indole-2-carbaldehyde (190 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (10 mg) in ethanol was heated in a sealed tube at 95 C. for 4 hours. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven for overnight to give 4-methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one. 1H NMR (360 MHz, DMSO-d6) delta13.07 (s, br, 1H, NH), 11.0 (s, br, 1H, NH), 7.78 (s, 1H, H-vinyl), 7.64 (d, J=8 Hz, 1H), 7.51 (d, J=8 Hz, 1H), 7.27 (dt, J=1, 8 Hz, 1H), 7.04-7.12 (m, 2H), 6.85 (d, J=8 Hz, 1H), 6.78 (d, J=8 Hz, 1H), 2.64 (s, 3H, CH3), 2.52 (s, 3H, CH3). MS El 288.

Statistics shows that 4-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 13220-46-7.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64483-69-8, name is 5-Acetylindolin-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 64483-69-8, Application In Synthesis of 5-Acetylindolin-2-one

5-Ethyl-2-oxindole To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid.

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

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); 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 141452-01-9 as follows. HPLC of Formula: C10H11NO2

1.26 g (5.8 mmoles) of di-tert-butyldicarbonate and 0.80 ml (5.8 mmoles) of Et3N are added successively at 20 C. to a solution of 0.85 g (4.8 mmoles) of methyl 5-indolinecarboxylate (J Heterocycl Chem (1993) 30 (4), 1133-1136) in 15 ml of CH2Cl2. The reaction mixture is stirred for 20 hours and concentrated to dryness under vacuum. The residue is divided between 50 ml of AcOEt and 25 ml of water. After stirring and decanting, the organic phase is washed with 25 ml of salt water, dried over MgSO4, filtered and concentrated to dryness under vacuum. The powder obtained is suspended in heptane, stirred and filtered in order to produce a white solid with a yield of 73%. Melting point=107-107.5 C.

According to the analysis of related databases, 141452-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6747024; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)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. SDS of cas: 3891-07-4

To a solution of 4a (1.88 g, 20 mmol), N-(2-hydroxyethyl)phthalimide (3.82 g, 20 mmol) and triphenylphosphine (7.87 g, 30 mmol) in tetrahydrofuran (30 mL) was added dropwise a solution of diethyl azodicarboxylate (4.7 mL, 30 mmol) in tetrahydrofuran (10 mL) at 0C over 0.5 h. The mixture was stirred at the same temperature for 6h and concentrated under reduced pressure. The residue was diluted in diethyl ether and stirred at -5 to 0C for 30 min and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel), eluting with petroleum ether and ethyl acetate (6:1, v/v) to give 5a (5.02g, 94 %) as a off-white solid.

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

Reference:
Article; Wang, Minghua; Ye, Cheng; Liu, Mingliang; Wu, Zhaoyang; Li, Linhu; Wang, Chunlan; Liu, Xiujun; Guo, Huiyuan; Bioorganic and Medicinal Chemistry Letters; vol. 25; 14; (2015); p. 2782 – 2787;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

603-62-3, name is 3-Nitrophthalimide, 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. name: 3-Nitrophthalimide

General procedure: 1 [43] (500 mmol) and 2 (500 mmol) were dissolved in acetonitrile(50 mL), then Cs2CO3 (204 mg, 625 mmol) was added in abovesolution. The resulting mixture was stirring overnight at roomtemperature under an inert atmosphere. After the reactioncompleted, the solvent was removed under vacuum and the residue was purified by silica gel column chromatography (petroleumether/ethyl acetate, 3/1, v/v).HP1, red solid, 93 mg, 36% yield;

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Biao; He, Zhaoshuai; Zhou, Hanxin; Zhang, Han; Li, Wu; Cheng, Tanyu; Liu, Guohua; Dyes and Pigments; vol. 146; (2017); p. 300 – 304;,
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. Product Details of 59-48-3

To a solution of oxindole (26 g) in 100 mL of concentrated sulfuric acid at -15 C. was added fuming nitric acid (8.4 mL) dropwise. Careful attention was paid to maintain the reaction temperature at -15 C. After the addition was complete, the reaction was stirred for 30 minutes and then poured into ice water. A yellow precipitate was formed which was isolated by filtration to provide 34 grams (98%) of 5-nitro oxindole.

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

Reference:
Patent; Pfizer Inc; US2005/256144; (2005); 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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H7NO2

The product of preparation 97 (5.0 g, 15 mmol), N-vinylphthalimide (2.62 g, 15.1 mmol), tri-ortho-tolylphosphine (473 mg, 1.55 mmol), palladium (II) acetate (98 mg, 0.4 mmol) and N, N-diisopropylethylamine (30 mL, 172 mmol) in acetonitrile (35 mL) was heated under reflux for 16 hours. The reaction mixture was then cooled to room temperature and the precipitate was filtered off. The solid was then dissolved in dichloromethane, activated charcoal was added, and the solution was filtered through CeliteNo.. The filtrate was concentrated in vacuo and the residue was re-crystallised from hot dichloromethane/methanol to afford the title compound as a yellow solid in 55% yield, 3.5 g. H NMR (400MHz, CDCI3) 6 : 2.20 (6H, s), 3.80 (2H, s), 4.30 (2H, d), 6.0 (1H, brs), 6.90 (2H, m), 7.01 (1H, m), 7.18 (1H, m), 7.26-7. 40 (4H, m), 7. 56-7. 61 (1 H, m), 7.75 (2H, m), 7.88 (2H, m)

According to the analysis of related databases, 3485-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/92840; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15861-23-1, name is Indoline-5-carbonitrile, 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 15861-23-1, name: Indoline-5-carbonitrile

A mixture of the compound of Part D (0.3 g, 0.72 mol) and 5-cyanoindoline (0.1 g, 0.694 mmol) in 2.5 mL 1,2-dichloroethane was stirred under N2 for 10 min, followed by the addition of sodium triacetoxyborohydride (0.22 g, 1.04 mmol, 1.5 eq.). The mixture was then stirred overnight at rt. The reaction was quenched by addition of water and 1M NaOH and extracted 3¡Á with CH2Cl2. Extracts were combined, washed with brine and dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 75:25) provided the desired alkylated product as a white foam (120 mg, 32%). 1HNMR (300 MHz, CDCl3) delta 8.27 (s, 1H); 7.93 (d, 1H); 7.30 (6H, m); 7.13-7.02 (6H, m); 6.18 (1H, bt), 5.88 (d, 1H, J=6 Hz); 5.03 (2H, dd, J=18, 10.8); 3.96, (s, 2H); 3.32 (t, 2H, J=6 Hz); 2.81 (t, 2H, J=6 Hz); 1.92 (m, 1H); 1.00 (6H, d, J=6.6 Hz). MS m/z 544.3 (M+H)+.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

13220-46-7, name is 4-Methylindolin-2-one, 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. Safety of 4-Methylindolin-2-one

(S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 78f (40 mg, 0.12 mmol 1) and 4-methyl-1,3-dihydro-indol-2-one (18 mg, 0.12 mmol) were dissolved in 1.5 ml of ethanol, and added with 6mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45C for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml¡Á2) and dried to obtain the title compound (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylide ne)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 83 (35 mg, yield 63.6%) as a yellow solid. MSm/z(ESI): 465.2(M+1) 1NMR(400 MHz, DMSO-d6) delta13.715(s, 1H, pyrrole-NH),10.934(s, 1H, indole-NH),7.572(s, 1H, -CH=C), 7.057 (t, 1H, -ArH), 6.840?6.821(d, 1H, -ArH), 6.790?6.771(d, 1H, -ArH), 4.737?4.725(d, 1H, -OH), 3.92(m, 1H, -CHOH), 3.75 (dd, 1H, seven-membered ring intra amide -NCH2), 3.58(t, 4H, morpholin2¡Á-CH2O), 3.441 (m, 2H, seven-membered ring -NCH2), 3.15(m, 1H, seven-membered ring outer amide-NCH2), 2.939(t, 2H, -CH2CH=C), 2.594(s, 3H, pyrrole-CH3), 2.426 (m, 4H, morpholin intra 2¡Á-CH2N), 2.388(s, 3H, pyrrole-CH3), 2.309?2.293(m, 2H, morpholin outer-NCH2), 2.078(m, 2H, seven-membered ring CH2-CH2-CH2)

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 39603-24-2, 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. 39603-24-2 name is 5,7-Dimethylindoline-2,3-dione, 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: Isatin (1mmol), 1,3-indanedione (1mmol), ethyl acetoacetate (1mmol), and NH4OAc (1mmol) were placed in a 25-mL round-bottomed flask in ethanol:water (9:1) (5mL). The resulting mixture was stirred at room temperature for time mentioned in Table 2, until completion of the reaction as monitored by thin-layer chromatography (TLC). After completion of the reaction, the mixture was filtered and washed with a small quantity of ethanol to furnish pure spiro[4H-indeno-[1,2-b]pyridine-4,3′-[3H]indoles]. The structure of products was confirmed by IR, 1H and 13C NMR, GCMS, HRMS, and elemental analysis.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,7-Dimethylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Dige, Nilam C.; Pore, Dattaprasad M.; Synthetic Communications; vol. 45; 21; (2015); p. 2498 – 2510;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem