Category: indolines-derivatives

Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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: 132898-96-5

General procedure: A mixture of cis-N-benzyl-2,5-bis(methoxymethyl)pyrrolidine (18a) (620 mg, 2.49 mmol, 1.00 equiv.) and 10% Pd/C (62 mg, 10% w/w) in MeOH (12 mL) was stirred in an autoclave at ambient temperature under H2 atmosphere (20 atm) for 6 h. After this time, the mixture was filtered through Celite and washed again with MeOH. The solvent was removed under reduced pressure to obtain the corresponding unprotected bis(methoxymethyl)pyrrolidine as a light yellow oil. The solution of obtained free amine cis-2,5-bis(methoxymethyl)pyrrolidine and DIPEA (766 muL, 4.40 mmol, 2.00 equiv.) in CHCl3 (5 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.08 g, 4.40 mmol, 2.00 equiv.) in CHCl3/THF (1:1, 50 mL) at room temperature. The resulting mixture was stirred further for 2 h and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 90% EtOAc in cyclohexane) to yield a yellow solid (723 mg, 1.96 mmol, 89%). M.p. 168 C. 1H NMR (400 MHz, DMSO-d6): delta = 11.46 (br s, 1H, 1-NH), 8.05 (dd, 3JH,H = 8.3 Hz, 4JH,H = 2.0 Hz, 1H, 6-CH), 7.80 (d, 4JH,H = 1.9 Hz, 1H, 4-CH), 7.09 (d, 3JH,H = 8.3 Hz, 1H, 7-CH), 3.73-3.58 (m, 2H, 12-CH, 15-CH), 3.52-3.20 (m, 4H, 16-CH2, 19-CH2), 3.37 (s, 6H, 18-CH3, 21-CH3), 1.78-1.62 (m, 2H, 13-CHa, 14-CHa), 1.57-1.37 (m, 2H, 13-CHb, 14-CHb) ppm. 13C NMR (100 MHz, DMSO-d6): delta = 182.9 (3-CO), 159.4 (2-CO), 153.6 (8-CN), 136.7 (6-CH), 130.8 (5-CSO2), 123.1 (4-CH), 118.1 (9-CCO), 112.7 (7-CH), 74.4 (2C, 16-CH2, 19-CH2), 59.9 (2C, 12-CH, 15-CH), 58.4 (2C, 18-CH3, 21-CH3), 26.9 (2C, 13-CH2, 14-CH2) ppm. HRMS (ESI+, MeOH): m/z = 391.0931 [M + Na]+, 423.1194 [M + Na + MeOH]+; calcd. 391.0934 for C16H20N2O6S + Na, 423.1196 for C16H20N2O6S + Na + MeOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 132898-96-5, its application will become more common.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 132898-96-5, A common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

The synthetic route of 132898-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The synthesis of 2-(6-(indolin-1 -yl)-6-oxohexyl)phthalimide 5.2.4 was performed following the report of Krasnov and co-workers ( see Krasnov et al., Mendeleev Commun. 25:412 (2015)): To a stirred solution of aniline (1 .0 equiv) and A/,A/-diethylaniline (1 .0 equiv) in 0.2 M dry CH2CI2was added a 0.2 M solution of acid chloride (1 .0 equiv) in dry CH2CI2dropwise over 10 min. After stirring at room temperature for 16 h, a 1 .0 N aq soln of HCI was added to the reaction mixture. After 30 min, the reactives were diluted with 20 ml. of EtOAc and washed with 2 c 20 ml. of water and 20 ml. of a 5% aq soln of NaHC03. The resulting organic phase was dried over Na2S04, filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by MPLC to afford the product.

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

Reference:
Patent; THE BOARO OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; THE TRUSTEES OF INDIANA UNIVERSITY; DRIVER, Tom, G.; MACHADO, Roberto, F.; SU, Naijing; GUAN, Xinyu; MAZUMDAR, Wrickban; RATIA, Kira; HICKOK, Jason, Ralph; LOCKETT, Angelia, Denise; (159 pag.)WO2019/153007; (2019); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 22190-33-6, These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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.

Step 2. tert-Butyl-5-bromoindoline-1-carboxylate (BI12) To a stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2¡Á). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as a off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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.

To a mixture of 6-bromoisatin (0.88 mmol) in AcOH (9 ml), Br2 (0.88 mmol) was added and the mixture was stirred for 48 h at reflux. After this time the reaction was cooled at 0 C, and the solid residue was paper filtered off, washed with AcOH and dried in the oven. The crude product was then recrystallized from AcOH to give the pure orange coloured product 1, 57%; mp >270 C with decomposition. 1H NMR, 300 MHz, DMSO-d6 delta = 7.23 (1H, s, H7); 7.82 (1H, s, C4), 11.22 (1H, brs, NH). 13C NMR, 75 MHz, DMSO-d6 delta = 117.40, 117.64, 119.61, 129.33, 133.81, 150.67, 159.83, 183.12.

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

Reference:
Article; Mollica, Adriano; Stefanucci, Azzurra; Feliciani, Federica; Lucente, Gino; Pinnen, Francesco; Tetrahedron Letters; vol. 52; 20; (2011); p. 2583 – 2585;,
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. 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6ClNO2

C. 5-Chloro-7-methyl-1 H-indole5-Chloro-7-methyl-1 H-indole-2,3-dione (1.8g, 9.23mmol) is added neat to a 1.0 M solution of lithium aluminum hydride in ether (92mL). The reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched with ice and is diluted with ethyl acetate (60OmL). The organic phase is collected, washed with sat NH4CI (2 XI OOmL) and brine (50 mL). The organic is dried over magnesium sulfate, filtered and concentrated in vacuo to give the crude product. Purification by flashchromatography on SiO2 eluting with 5% ethyl acetate/ heptane gives 1.27 g, (83% yield) of desired product. 1H-NMR (CDCI3, 300 MHz): delta 8.1 (bs, H), 7.45 (s, 1 H), 7.2 (d, 1 H), 7.0 (s, 1 H), 6.5 (d, H), 2.5 (s, 3H). LCMS m/z: [M+H]+=166

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; CHOI-SLEDESKI, Yong-Mi; GARDNER, Charles, J.; LIANG, Guyan; POLI, Gregory, B.; SHUM, Patrick, Wai-Kwok; STOKLOSA, Gregory, T.; ZHAO, Zhicheng; WO2011/22449; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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 2058-72-2, Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

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; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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. HPLC of Formula: C9H6BrNO2

General procedure: A mixture of corresponding compound 1(0.5 mmol), isatin 3 (0.5 mmol), and sarcosine (0.5 mmol) in acetonitrile (40 mL) (for 1a-c) or in amixture of acetonitrile (30 mL) and chloroform (10 ml) (for 1d-f) was refluxed with stirring for 36 or 72 h for starting compounds 1a-c and 1d-f, respectively. Then the reaction mixture was cooled to room temperature, the precipitate of compounds 4a-e,j,o was filtered off and washed with acetonitrile and water. The reaction mixture of compounds 4f-i,k-n,p-t was concentrated on a rotary evaporator to half of an original volume. After cooling, the precipitate was filtered off and washed with water. Recrystallization from acetonitrile or methanol (4n) gave dispirocompounds 4a-t.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-72-2, its application will become more common.

Reference:
Article; Izmest’ev, Alexei N.; Gazieva, Galina A.; Sigay, Natalya V.; Serkov, Sergei A.; Karnoukhova, Valentina A.; Kachala, Vadim V.; Shashkov, Alexander S.; Zanin, Igor E.; Kravchenko, Angelina N.; Makhova, Nina N.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2240 – 2249;,
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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H4ClNO2

In a 100 mL round bottom flask, according to the feed ratio (7-chloroisatin: methanol (1:1.5); 7-chloroisatin: 1,3-diphenylpropanedione (1:1.2))Add 7-chloroisatin 80 mg (0.44 mmol), methanol 21.1 mg (0.66 mmol) and 1,3-diphenylpropanedione 118.7 mg (0.53 mmol), respectively.A catalytic amount (0.1-fold equivalent of 7-chloroisatin) was added to 001¡Á7FC, ferrocene and palladium acetate, and 25 mL of solvent tetrahydrofuran was heated to 90 ¡ã C, and the reaction was heated for 6 hours.The reaction was monitored by thin layer chromatography. After the reaction was completed, the heating was stopped, the condensing device was removed, the mixed system was concentrated under reduced pressure, and purified by column chromatography.The title compound (8) was obtained by drying to give 83.3 mg,yield of 76percent.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Tian Danni; Ding Shunjun; Wang Xuechuan; Dong Hao; Wang Qiang; (15 pag.)CN108395438; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 16800-68-3, The chemical industry reduces the impact on the environment during synthesis 16800-68-3, name is 1-Acetylindolin-3-one, I believe this compound will play a more active role in future production and life.

3 – (4 -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, 31 mg and gave rise 62% to unit_.

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-Acetylindolin-3-one, other downstream synthetic routes, hurry up and to see.

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