Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 22120-50-9, name is 2,3-Dimethylindoline, 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 22120-50-9, Safety of 2,3-Dimethylindoline

A mixture of 2,3-dimethylindoline (0.10 g, 0.679 mmol) and 2-bromoethanamine hydrobromide(0.153 g, 0.747 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HCl and purifiedby preparative HPLC to give the title compound as a mixture of cis and trans ismoers that was notpurified further (128 mg). LCMS m/z = 191.2 [M+H]+.

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, 2,3-Dimethylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
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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 6941-75-9 as follows. SDS of cas: 6941-75-9

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
Indoline – Wikipedia,
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Reference of 71294-07-0, These common heterocyclic compound, 71294-07-0, name is 5,6-Difluoroindolin-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.

Preparation of (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one To a solution of 5,6-difluorooxindole (450 mg, 2.66 mmol) in THF (20 mL) at 0 C., was added 1 M LiHMDS in THF (5.3 mL, 5.3 mmol). The reaction mixture was stirred at 0 C. for 10 minutes. 4-bromo-5,5-dimethyl-5H-furan-2-one (340 mg, 1.78 mmol) was then added. The reaction mixture was stirred at 0 C. for 30 min., and then at room temperature for an additional 30 min and quenched with 2.5M aqueous H2SO4 (3 mL). The resulting mixture was stirred at room temperature for 16 hours and poured into water (100 mL). The precipitates were filtered, washed with water and dried in vacuo to yield (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-5,6-difluoro-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 547 mg, 90%. 1H NMR (300 MHz, d6-DMSO) delta ppm 1.58 (s, 6 H) 6.81 (dd, J=10.55, 6.74 Hz, 1 H) 7.45 (dd, J=10.55, 8.21 Hz, 1 H) 7.54 (s, 1 H) 10.44 (s, 1 H)

Statistics shows that 5,6-Difluoroindolin-2-one is playing an increasingly important role. we look forward to future research findings about 71294-07-0.

Reference:
Patent; ALLERGAN, INC.; US2007/173500; (2007); A1;,
Indoline – Wikipedia,
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Application 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.

Octan -2 -acetylenic acid 4 – nitrophenyl-unit (78.3 mg 0.3 mmol), was used. 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 3h 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, 38 mg and gave rise 87% to unit_.

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

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
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Synthetic Route of 6326-79-0,Some common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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.

A chilled (O 0C) aqueous solution of NaNO2 (6.1 g, 88.5 mmol, 27 mL of water) was added to a chilled (0 “C) solution of commercially available compound HI (20 g, 88.5 mmol) in aqueous NaOH (96 mL, 96 mmol, 1 N). The combined solutions were added slowly to chilled aqueous H2SO4 (9.2 mL of cone. H2SO4, 80 mL of water) by means of an addition funnel with the tip below the surface of the acid solution Ice was added to the reaction to maintain 0 ‘C and ether was added to control foaming, as needed. After stirring an additional 10 min, the diazonium solution was added slowly to a chilled mixture of SnCI2-2H2O (50 g, 221 mmol) in concentrated HCI (80 mL) by means of an addition funnel with the tip below the surface of the acid solution. Ice was added to the reaction to maintain 0 C and ether was added to control foaming, as needed. After stirring an additional hour at 0 C, the reaction mixture was stirred at room temperature overnight. Filtered, the golden yellow powder was dissolved in aqueous NaOH, washed with ether, precipitated with aqueous HCI, filtered, and dried to give 20 g of crude compound H2 as yellow powder used into the following reaction without the further purification.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; KREMOSER, Claus; ABEL, Ulrich; STEENECK, Christoph; KINZEL, Olaf; WO2011/20615; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

Example 51 5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid (2-diethylamino-ethyl)amide 5-Bromo-1,3-dihydroindol-2-one (0.17 g, 0.8 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide (0.2 g) to give 0.09 g (26%) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.61 (s, br, 1H, NH), 10.98 (, br, 1H, NH), 8.09 (d, J=1.7 Hz, 1H, H-4), 7.76 (s, 1H, H-vinyl), 7.42 (t, J=5.5 Hz, 1H, CONHCH2), 7.24 (dd, J=1.7 & 8.0 Hz, 1H, H-6), 6.82 (d, J=8.0 Hz, 1H, H-7), 3.23-3.32 (m, 2H, NCH2), 2.46-2.55 (m, 6H, 3*NCH2), 2.43 (s, 3H, CH3), 2.42 (s, 3H, CH3), 0.96 (t, J=7.2 Hz, 6H, 2*NCH2CH3). MS-EI m/z 458 and 460 [M+-1 and 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 5-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; Pharmacia Corporation; US2003/216410; (2003); A1;,
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. 1498-88-0, name is 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline], A new synthetic method of this compound is introduced below., Quality Control of 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline]

1,3,3-Trimethyl-60-nitrospiro[chromene-2,20-indoline] (6.45 g,20 mmol) and SnCl2 (18.96 g, 0.10 mol) were added to a flask underN2 atmosphere. Anhydrous ethanol (100 mL) was added and thereaction mixture was heated to reflux for 2 h. After reaction themixture was cooled to room temperature and filtered. The filtratewas concentrated and 5% aqueous NaOH was added to the residue.The organic phase was extracted with dichloromethane for threetimes,washed withwater and dried. After filtration the solvent wasremoved by evaporation and the residue was purified by columnchromatography with petroleum ether/ethyl acetate (3:1, v/v) aseluent to give the reduction product 1,3,3-trimethyl-60-aminospiro[chromene-2,20-indoline] (3.18 g) as brown solid in 54% yield. Mp139e140 C. 1H NMR (400 MHz, CDCl3) d 7.16e7.14 (m, 1H), 7.05 (d,J 8.3 Hz, 1H), 6.81e6.79 (m, 1H), 6.74 (d, J 8.8 Hz, 1H), 6.55e6.44(m, 3H), 6.41 (d, J 7.9 Hz, 1H), 5.67 (d, J 10.9 Hz, 1H), 2.85 (s, 3H),1.45 (s, 3H), 1.30 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Zhang, Ruiqing; Hu, Luping; Xu, Zhenxiang; Song, Yanxi; Li, Hongqi; Zhang, Xin; Gao, Xucheng; Wang, Mengxuan; Xian, Chunying; Journal of Molecular Structure; vol. 1204; (2020);,
Indoline – Wikipedia,
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Electric Literature of 35197-64-9, 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 35197-64-9 as follows.

General procedure: In this work, previously reported N-benzyl-2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanamide derivatives (25a-e) [44] were obtained by activating the carboxylic acid group of 24 (1 eqv) by using n-propanephosphonic acid anhydride (T3P, 50% in EtOAc, 1 eqv). The reaction was carried out under argon atmosphere for 2hat 0C in dry methylene chloride. Then, distilled triethylamine (1.2 eqv) and the appropriate N-benzylamine (1.1 eqv) were added to the reaction mixture [57]. The reaction was continued at room temperature for 12h. The products were purified by column chromatography over silica gel (DCM/acetone=9:1) to yield 25a-e as a white solid.

According to the analysis of related databases, 35197-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; ?mudzki, Pawe?; Fija?kowski, ?ukasz; Furga?a, Anna; Gryz?o, Beata; Hoefner, Georg C.; Kulig, Katarzyna; Malawska, Barbara; Malawska, Katarzyna; Nowaczyk, Alicja; Podkowa, Adrian; Rapacz, Anna; Sa?at, Kinga; Wanner, Klaus T.; Zar?ba, Paula; European Journal of Medicinal Chemistry; vol. 188; (2020);,
Indoline – Wikipedia,
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Synthetic Route of 1201923-48-9, 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. 1201923-48-9 name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, 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.

To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 ml.) at RT was added 4M HCI in dioxane (56 ml_, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 ml.) affording the title compound (7.8 g,99%) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLIKE BEECHAM CORPORATION; WO2009/158371; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 13861-75-1, A common heterocyclic compound, 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, molecular formula is C10H9NO, 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: Spiro [cycJ.opropane-1, 3 ?-indoline]To mixture of spiro[cyclopropane-l, 3?-indoiine]-2?-one(35.0 g, 219.87 mmol) in THF? (750 mL) was slowly added lithiumaluminium hydride (2M solution in THF) (219.9 mL, 439.7 mrnol) at 0C. The resulting mixture was allowed to be warmed to room temperature and then heated to reflux for 18 hour under argon atmosphere. Upon completion as monitored by TLC, the reactionmixture was cooled to room temperature, quenched with ice, basified with aqueous ammonia, and extracted with ethyl acetate (2 x 750 mL) . The combined organic layers were washed. successively with water (100 rn) and brine (100 mL), dried over sodium sulfate and concentrated under vacuum to obtain acrude oily product (32 g, 100%) . The product was subjected tonext reaction without further purification.MS(ESI)m/z: 146.1[M+1] ; ?HNMR (400 MHz, DMSO-d6) : 5 0.88 (s, 4H)3.43 (S. 21-{), 5.54 (s, 1H), 6.44-6.55 (m, 3H), 6.85 (t, J =7.6 Hz, 1M).

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DESHPANDE, Anil M.; BARAWKAR, Dinesh; PATIL, Santosh; BANKAR, Digambar; (178 pag.)WO2016/88903; (2016); A1;,
Indoline – Wikipedia,
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