Category: indolines-derivatives

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 6941-75-9

A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g ,0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-l,3-dione (5 g, 22mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HC1. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2S04 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261C; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J = 9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]”); IR (thin film) 1684, 3246, 606 cm-1.

The synthetic route of 6941-75-9 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; WO2014/100206; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Computed Properties of C9H9NO

4-Methyl-1,3-dihydro-indol-2-one (189 mg), 147 mg of 6-methoxy-2-oxindole, and 1 drop of piperidine in 2 mL of ethanol were heated to 100 C. for 4 hrs. The reaction mixture was cooled and the precipitate was filtered, washed with cold ethanol and dried in a vacuum oven to give 221 mg of 4-methyl-3-(3-methyl-thiophen-2-ylmethylene)-1,3-dihydro-indol-2-one (Compound III) (87%) as a brown solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.53 (s, br, 1H, NH-1), 7.87 (s, 1H, H-vinyl), 7.75 (d, J=5.25 Hz, 1H, H-5′), 7.09-7.11 (m, 2H, H-6, 4′), 6.81 (d, J=7.66 Hz, 1H, H-5), 6.73 (d, J=7.77 (d, J=7.77 Hz, 1H, H-7), 2.60 (s, 3H, CH3-4), and 2.46 (s, 3H, CH3-3′).

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; Sugen, Inc.; US6846839; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 32692-19-6, 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. 32692-19-6 name is 5-Nitroindoline, 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: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Recommanded Product: 32692-19-6

Example 7 1-methylethyl 4-[4-(5-nitro-2,3-dihydro-1H-indol-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]piperidine-1-carboxylate; [Show Image] To a mixture of 5-nitro-2,3-dihydro-1H-indole (328 mg, 2.00 mmol), 1-methylethyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate (323 mg, 1.00 mmol) obtained in Reference Example 3, and N,N-dimethylformamide (10 mL) was added potassium carbonate (830 mg, 6.01 mmol), and the mixture was stirred at 100C for 2 days. The reaction mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated. The residue was crystallized from ethyl acetate to give the title compound as yellow crystals (175 mg, yield 39%). 1H-NMR (300 MHz, CDCl3)delta:1.28 (d, J = 6.0 Hz, 6 H), 1.82 – 1.99 (m, 2 H), 2.02 – 2.16 (m, 2 H), 2.91 – 3.08 (m, 2 H), 3.38 (t, J = 8.7 Hz, 2 H), 4.29 – 4.46 (m, 2 H), 4.65 (t, J = 8.7 Hz, 2 H), 4.87 – 5.02 (m, 2 H), 6.65 (d, J = 3.8 Hz, 1 H), 7.16 (d, J = 3.8 Hz, 1 H), 8.08 (s, 1 H), 8.17 (dd, J = 9.0, 2.3 Hz, 1 H), 8.57 (s, 1 H), 8.62 (d, J = 9.4 Hz, 1 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; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, name: Isoindoline

Example 137:; EPO 137To a dichloromethane solution (8 ml.) of phosgene (769 uL, 20% in toluene, 1.45 mmol) at -70C was added triethylamine (234 mg, 2.32 mmol) and isoindoline (138 mg, 1.16 mmol). The mixture was slowly warmed to room temperature and stirred for 1 hour. To the reaction mixture were added 103d (245 mg, 0.980 mmol), triethylamine (147 mg, 1.45 mmol) and 4-(dimethylamino)pyridine (18 mg, 0.15 mmol). The mixture was stirred at room temperature for 72h. It was then diluted with ethyl acetate (30 ml_) and washed with cold 1 M HCI (20 ml_), cold 1 M sodium bicarbonate (20 mL) and brine (20 mL), dried with Na2SO4 and concentrated. After column chromatography (20-40% ethyl acetate in hexane), the title compound was obtained in 57% yield. 1H NMR (CDCI3): delta 7.44 (1H, dd, J=8.6, 5.3Hz), 7.4-7.2 (4H, m), 7.03 (1 H, dd, J=9.8, 2.2Hz), 6.86 (1 H, m), 4.98 (1 H, m), 4.71 (4H, m), 4.25 (2H, m), 3.37 (2H, m), 1.28 (3H, t, J=7Hz). LCMS (APCI): 396.1 (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; PFIZER, INC.; WO2006/40646; (2006); 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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2O2

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5,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.

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 2,3-Dioxoindoline-5-sulfonyl chloride, 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

Reference of 193354-13-1, 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. 193354-13-1 name is 5-Iodoindolin-2-one, 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.

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 ML of methanol, 15 ML of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide.. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated.. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane).. The fractions containing product were concentrated and allowed to stand.. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

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

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

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

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

[0715] Step 12: Synthesis of S-(5-(1,3-dioxoisoindolin-2-yl)pentyl)ethanethioate (15-k) To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). 1H NMR (400 MHz, CDCl3): delta 7.84 (dd, J = 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J = 5.5 Hz, 3.1Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 2.85 (t, J = 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M++1).

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

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; LADNER, Robert D.; (345 pag.)WO2018/128720; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem