Indolines-derivatives

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. 199328-10-4, name is Methyl Oxindole-5-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Step 2: Synthesis of 5-Carboxy-2-oxindole. 5-Methoxycarbonyl-2-oxindole (1 g) and 1 g of sodium hydroxide in 20 mL of methanol was refluxed for 3 hours. The reaction mixture was cooled and concentrated to dryness. The residue was dissolved in water and extracted twice with ethyl acetate. The aqueous layer was acidified with 6 N hydrochloric acid and the precipitated solid collected, washed with water, and dried to give 0.7 g (78%) of the title compound as an off-white solid.

The synthetic route of 199328-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
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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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

A solution of 5-nitroindoline (1.033 g, 6.30 mmol), TEA (0.827g, 8.19 mmol) in DCM (30 mL) at 0C was slowly added methylsufonyl chloride (0.868 g, 7.56 mmol). The mixture was warmed up and stirred at room temperature for 0.5 h. The reaction was quenched with water (30 mL) and extracted with DCM (25 mL x4). The organic layers were combined, dried and concentrated under reduced pressure to afford crude 1 (1.427 g, 5.9 mmol, yield 95%), which was used for next step without further purification.

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:
Patent; ACEA BIOSCIENCES INC.; XU, Xiao; WANG, Xiaobo; MAO, Long; ZHAO, Li; XI, Biao; WO2015/6754; (2015); A2;,
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Synthetic Route of 6941-75-9, 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 6941-75-9 as follows.

(B) Synthesis of Compound 31-c 194 ml of fuming nitric acid (fum. HNO3) was added to 0.9 L of concentrated sulfuric acid under stirring and cooling in an ice water bath. The mixture was stirred for 1 hour under cooling in an ice water bath, and then 215 g of Compound 31-a was added slowly to the mixture in portions over 30 minutes, while an inside temperature was maintained at 15 C. or lower. After completion of the addition, the mixture was stirred at room temperature for 8 hours. The reaction liquid was poured into 1 L of ice water, to precipitate crystals. After stirring, the crystals were collected through filtration, and washed with running water. The thus-obtained crude crystals of Compound 31-b were transferred to another flask without purification. 1 L of DMF was added thereto, and the whole was stirred at room temperature. To the resultant suspension, 200 ml of 25% ammonia water was added under stirring, and the mixture was stirred at room temperature for 3 hours. The crystals were collected through filtration, and added to 1.5 L of isopropyl alcohol. The mixture was refluxed under heating for 30 minutes, and then stirred at room temperature for 3 hours. The crystals were collected through filtration, washed with running hexane, and dried, to thereby obtain 131 g (48% yield from Compound 31-a) of Compound 31-c.

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:
Patent; FUJI PHOTO FILM CO., LTD.; US2006/142553; (2006); A1;,
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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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(Bromomethyl)isoindoline-1,3-dione

0.021 mol (4.99 g) of 2-(bromomethyl)-1H-isoindole-1,3(2H)-dione ( Sigma-Aldrich) was added to a solution of 4.04 g (0.020 mol) of the compound XA0 obtained in substage 1.1) of Example 1 in 35 ml of acetone (Sigma-Aldrich), in an ice bath (highly exothermic reaction). Once the addition was complete, the reaction medium was stirred at ambient temperature for 3 hours and then filtered. The filtrate was concentrated under vacuum in order to obtain the expected product XA2 in the form of a yellow oil (5.84 g, yield 91%) which will be used in the following stage without purification.

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:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE TOULOUSE III – Paul Sabatier; COUTELIER, Olivier; DESTARAC, Mathias; LANGLAIS, Marvin; (16 pag.)US2019/359603; (2019); A1;,
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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;,
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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;,
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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);,
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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);,
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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;,
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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;,
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