Category: 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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Nitroindolin-2-one

Step-b: tert-butyl 5-nitro-2-oxoindoline-l-carboxylate: Di-tert-butyl dicarbonate (4.63 g, 21.2 mmol) and sodium hydrogen carbonate (10.7 g, 127 mmol) were added to a stirred solution of 5-nitroindoIin-2-one (3.0 g, 14.2 mmol) in THF (150 mL) and the mixture was heated to 60C. After 3h, the reaction mixture was cooled, filtered and the filtrate was concentrated under reduced pressure. The obtained crude was purified by chromatography by using silica gel using a mixture of 10% ethyl acetate/hexane as an eluent to get the desired compound as a white solid as (2.3 g, 51%). 1H-NMR (300 MHz, DMSO-i/6): delta 8.3 (d, 1H), 8.2 (s, 1H), 7.9 (d, 2H), 3.8 (s, 2H), 1.5 (s, 9H).

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; ORION CORPORATION; UJJINAMATADA, Ravi Kotrabasaiah; HOSAHALLI, Subramanya; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; WO2015/92118; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 350797-56-7, name is 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate, 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 350797-56-7, HPLC of Formula: C22H23N3O4

Procedure-2: To a stirring solution of 3-(7-Cyano-5-(2-nitropropyl)-indolin-l-yl)- propyl benzoate of Formula XII (10 g, 25.4mmol) in methanol (50 ml) was added con. HC1 (10 ml) followed by Zn (3.35 g, 50.08mmol). The mixture was heated to 60-65 C for 20 h. After completion of the reaction, the mixture was filtered and the residue was washed with Methanol (5 ml). The filtrate was concentrated under vacuum and the residue was dissolved in water and washed with isopropyl ether (2×20 ml). The MDC (80 ml) was added to the aqueous layer and basified the mixture by adding aqueous 20% NaOH solution. The obtained solid slurry mass was filtered and both the layers were separated from the filtrate. The organic layer was washed twice with water (2 x 100 ml) and concentrated under vacuum to get 8.5 g of 3-(5-(2-aminopropyl)-7- cyanoindolin-l-yl)propyl benzoate of Formula XII as a thick mass (HPLC purity is -abo-ve-95-%).

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, 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PANACEA BIOTEC LTD; JAIN, Rajesh; RAO, Jagadeeshwar R; RAO, Siripragada Mahender; WO2012/131710; (2012); A2;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H4F3NO3

3beta-hydroxy-5alpha,8alpha-peroxyandrost-6-ene-17-hydrazine obtained in the step (f)(100 mg, 0.30 mmol) and 5-trifluoromethoxy-isatin (76.2 mg, 0.30 mmol) dissolved in 20 mLIn absolute ethanol, placed in a 50 mL single-necked flask, and the system was heated to 50 C for 2 to 4 hours.The reaction was terminated until no starting material was reacted. Decomposition under reduced pressure, purification by silica gel column,The product was obtained as a pale yellow solid, 114.2 mg, yield: 70%.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qiqihar Medical University; Bu Ming; Wang Haijun; Wang Jing; Lin Yu; Li Hongling; Ma Yukun; (18 pag.)CN108707180; (2018); 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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrNO

TDI01239-1 (500 mg, 2.358 mmol) was dissolved in tetrahydrofuran (24 mL), and cooled to 0 C. Under the protection of nitrogen, 60% NaH (236 mg, 5.895 mmol) was added to the above reaction solution, and the reaction was performed at room temperature for 1h after the addition. Bromoethyl acetate was then added at 0 C, and the reaction was continued at room temperature for 2h. LC-MS indicated the reaction was complete. After completion of the reaction, ice water and 1N HCl solution was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate (15 mL). The combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to dryness to afford TDI01239-2 (700 mg, yellow solid, yield: 99.57%). MS m/z (ESI): 298.1 [M+H].

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; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (106 pag.)EP3421464; (2019); A1;,
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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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

(c) Methyl 4-methoxy-anthranilate One hundred fifty-eight grams (0.89 mol) of 6-methoxy-isatine are suspended in 1300 ml of methanol and mixed with a solution of 54 gm (1.34 mol) of sodium ethoxide in 500 ml of methanol. One hundred eight milliliters (1.07 mol) of 30% hydrogen peroxide are added thereto dropwise, under stirring, and the resulting mixture is stirred for 30 minutes. The contents of the flask are concentrated down to half their volume, mixed with water, and adjusted to a pH of 5 to 6 with glacial acetic acid. After extraction with methylene chloride, the mixture is subjected to suction filtration, kieselguhr being used, and dried with sodium sulfate, and the solvent is distilled off. The residue is recrystallized from petroleum ether/cyclohexane (2:1). M.p: 80-82 C., Yield: 109 gm (67.7% of theory). The following compounds are prepared by analogous procedures:

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 52351-75-4.

Reference:
Patent; Dr. Karl Thomae GmbH; US4518597; (1985); A;,
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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. 924304-73-4, name is 4-Chloroisoindoline hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H9Cl2N

Step 3: Synthesis of (2Jff,65>,13a5′,14ai?,16a5rZ)-ethyI 6-(tert-butoxycarbonylamino)-2-(4- chloroisoindoline-2~carbonyloxy)-5,16-dioxo-2,3,5,6,7,8,9,ll,13a,14,14a,15,16,16a- tetradecahydro-lH-cyclopropa(e)pyrrolo[2,l-i][l,7,10joxadiazacyclopentadecine-14a- carboxylate[0472] (2R,6S, 13aS, 14aR, 16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy- 5,16-dioxo~2,3,5,6,7,8,9,l l,13a,14,14a,15,16,16a4etradecahydro-1H- cyclopropa(e)pyrrolo[2,l-/][l,7,10]oxadiazacyciopentadecine-14a-carboxylate (0.30 g, 0.61 mmol) in toluene (5 mL) was added lj ‘-carbonyldiimidazole (0.12 g, 0.73 ramol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2-amine (0.53 mL, 3.0 mmol), followed by 4- chloroisoindoline hydrochloride salts (0.15 g, 0.79 mmol). The reaction was stirred at 60 C for 3 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (etaexanerEthyl acetate=l:3) to give (2/?,65,13a5,14aR,16a5’,Z)-ethyI 6-{tert- butoxycarbonylamino)-2-(4-chloroisoindoline-2-carbonyloxy)-5,16-dioxo- 2,3,5,6,7,8,9,11, 13a,14,14a,15,16,16a-tetradecahydro-1H-cyclopropa(phiyrrolo[2,l- /][l,7,10]oxadiazacyclopentadecine-14a-carboxylate as white solid (0.18 g, 86%). MS: Calcd.: 674.3; Found: [M+eta]+ 675.1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 924304-73-4.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA, INC.; WO2008/137779; (2008); A2;,
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2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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. category: indolines-derivatives

General procedure: To a hot stirred solution of the key intermediates 3a, b (0.27 gm,1 mmol) and sodium acetate (0.16 gm, 2 mmol) in acetic acid(15 mL), N-substituted isatins 6a-f were added and this mixturewas heated under reflux for 3 h. The formed solidwas filtered whilehot, dried and recrystallized from DMF/ethanol to obtain the targetcompounds 7a-g.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Eldehna, Wagdy M.; Abo-Ashour, Mahmoud F.; Nocentini, Alessio; Gratteri, Paola; Eissa, Ibrahim H.; Fares, Mohamed; Ismael, Omnia E.; Ghabbour, Hazem A.; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 250 – 262;,
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39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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. SDS of cas: 39603-24-2

General procedure: To a mixture of isatin(s)/acenaphthoquinone/cyclic ketone(s) (1 mmol) and anthranilamide (1mmol) in ethanol(96%, 2 mL), sulfamic acid (0.2 mmol) was added. Thereaction mixture was stirred at ambient temperature forthe time mentioned in table 2 until completion of reaction,as monitored by TLC. After the completion ofreaction, the precipitated products was just filtered. Theconfirmation of isolated products was done by spectraltechniques such as 1H, 13C NMR, IR and massspectrometry.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mane, Mansing M.; Pore, Dattaprasad M.; Journal of Chemical Sciences; vol. 128; 4; (2016); p. 657 – 662;,
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Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-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. Recommanded Product: 5-Bromoisoindolin-1-one

A solution of 5-bromoisoindolin-l-one (10 g, 47.16 mmol) in dioxane (450 mL) was degassed before Xantphos (2.73 g, 4.72 mmol), DIPEA (9.88 mL, 56.59 mmol), Pd2(dba)3 (2.159 g, 2.36 mmol) and methyl 3-mercaptopropanoate (32.6 mL, 330.12 mmol) wasadded. The reaction was heated to 80 C for lh. The reaction was concentrated in vacuo. Approximately half of the material was purified by flash chromatography eluting with 0- 5% methanol in EtOAc to afford 4.69g of product. Only half the material was purified this way because the crude material solidified part way through loading onto the column. The solidified material was triturated with methanol and 4.48 g of product was collected byfiltration as a colorless solid. The mother liquor was concentrated in vacuo and purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 1. lg product. This was combined with the material from the first column to give l0.27g (86%) of the title compound.LC/MS: m/zrr252 [M+H]. ?H NMR (500 MHz, DMSO-d6) i5 2.69 (t, 2H), 3.26 (t, 2H),3.60 (s, 3H), 4.34 (s, 2H), 7.38 (d, 1H), 7.52 (s, 1H), 7.58 (d, 1H), 8.48 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 552330-86-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; LEVER, Sarah; NARJES, Frank; OLSSON, Roine, Ingemar; VON BERG, Stefan; (124 pag.)WO2018/229155; (2018); A1;,
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Synthetic Route of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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 solution of oxindole (4.43 g, 33.3 mmol) in AcOH (35 mL) was added NIS (9 g, 40.0 mmol) at rt. The mixture was stirred for 1.5 hours at which point water (60 mL) was slowly added dropwise, followed by about 5 mL of EtOAc to solubilize impurities. The solid was filtered, washed with a small amount of EtOAc followed by diethyl ether, to give 5-iodo-oxindole (5.4 g, 62%) as a light pink solid clean by proton NMR in DMSO.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
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