Indolines-derivatives

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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

5-Ethyl-2-oxindole To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Related Products of 39603-24-2, These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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.

Will be perchloric acid (70%, 1 mmol, 142 mg) was added 5-methoxyisatin (1 mmol, 177 mg), 2-amino-5-chloro-pyridine (1.35 mmol, 174 mg) And tert-butylisocyanide (1.35 mmol, 112 mg) in n-butanol (4 mL) The reaction was stirred at reflux for 8 hours. When the reaction solution was cooled to room temperature, Filtration and washing the filter cake with a small amount of ethanol gave the desired product in 39% yield.

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

Reference:
Patent; Guangdong South China New Drug Initiative Center; Lin Shuo; Che Chao; Li Song; Yang Bo; Xin Shengchang; (18 pag.)CN105017253; (2017); B;,
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Application of 3676-85-5, 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. 3676-85-5 name is 5-Aminoisoindoline-1,3-dione, 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.

Example 90 N-(2,6-Difluorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (162 mg, 0.59 mmol, 1.2 eq) and triethylamine (60 mg, 0.59 mmol, 1.2 eq) were added to a solution of 2,6-difluorophenylacetic acid (101 mg, 0.49 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (80 mg, 0.49 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with achloroform/methanol solution to give the title compound as a crystal (10 mg, 6.1%). MS m/z: 331 1H-NMR delta: 4.64 (2H, d, J = 4.64 Hz), 6.88 (1H, t, J = 5.73 Hz), 7.11 (2H, t, J = 8.05 Hz), 7.56 (1H, dd, J = 1.83, 8.29 Hz), 7.66 (1H, d, J = 8.29 Hz), 7.98 (1H, d, J = 1.71 Hz), 9.15 (1H, s), 11.08 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
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Reference of 2913-97-5, These common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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.

Compound 2: NaBH(OAc)3 (3,05 g ;14,4 mmol) was added to a solution of N-ethylaniline (1,16 g ; 9,6 mmol) and 2-phthalimidoacetaldehyde (1) (2,72 g, 14,4 mmol) in CH2Cl2 (28 mL). After 24 h at 20°C, CH2Cl2 was added and the organic phase was washed with H2O, dried (MgSO4) and evaporated. The crude product was purified by chromatography over silica gel (80:20 CH2Cl2-cyclohexane) to afford 2 as a yellow solid (2,71 g, 96 percent). 1H NMR (250 MHz, CDCl3): delta 7,85 (m, 2H), 7,71 (m, 2H), 7.24 (t, J = 7,8 Hz, 2H), 6,86 (d, J = 7,8 Hz, 2H), 6.67 (t, J = 7,8 Hz, 1H), 3.91 (dd, J = 6,5, 8,1 Hz, 2H), 3,58 (dd, J = 6,5, 8,1 Hz, 2H), 3,46 (q, J = 6,9 Hz, 2H), 1.22 (t, J = 7,0 Hz, 3H). 13C NMR (63 MHz, CDCl3): delta 168,0 (C), 147,2 (C), 133,7 (CH), 131,8 (C), 129,2 (CH), 123,0 (CH), 116,0 (CH), 111,9 (CH), 47,8 (CH2), 44,6 (CH2), 35,0 (CH2), 12,2 (CH3). MS: m/z = 295 (MH+). Anal. calcd for C18H18N2O2 (294,14), C 73.45, H 6,16, N 9,52. Found C 73,33, H 6,17, N 9,62.

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universite Paris Descartes; EP2537855; (2012); A1;,
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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;,
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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;,
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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

Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Application In Synthesis of N-(5-Bromopentyl)phthalimide

General procedure: To a suspension of compound 9-12 and potassium carbonate in ACN, was added dropwise N-methylbenzylamine or piperidine under stirring and the reaction mixture was refluxed for 24 h. The reaction mixture was cooled and filtered. After evaporation of the filtrate, purification by column chromatography on silica gel (cyclohexane/EtOAc/TEA) yielded compounds 16 and 17.

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, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
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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. 6341-92-0, name is 6-Chloroisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4ClNO2

In 25 ml sealed tube by adding 1 a (0.5 mmol, 88.6 mg), 2 h (0.5 mmol, 90.8 mg), iodine simple substance (0.25 mmol, 63.5 mg), triethylamine (0.25 mmol, 25.3 mg) and chlorobenzene (2 ml), then put into 130 C in oil bath stirring reaction 10 h. Add 50 ml water quenching reaction, extracted with ethyl acetate (50 ml × 3), the organic phase after the mass concentration is 10% of Na2 S2 O3 Solution and saturated salt water are successively washing, drying with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to obtain the target product 3 t (115.9 mg, 82%). The compound of the characterization data are as follows

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; Xinxiang Medical University; Gao Qinghe; Liu Xingxia; Liu Zhaomin; Yang Limin; Yuan Huan; He Shuang; (16 pag.)CN107501180; (2017); 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 169037-23-4

Step 1. Preparation of 2-amino-5-(trifluoromethoxy)benzoic Acid 5-(Trifluoromethoxy)isatin (15.0 g, 65 mmol) and potassium hydroxide pellets (4 g) were mixed in water (35 mL) and cooled to 0 C. With vigorous stirring, a solution of 30% aqueous hydrogen peroxide (11.7 g), potassium hydroxide pellets (5.8 g), and water (80 mL) was added drop-wise keeping the temperature below 10 C. After stirring 1 hour at 0 C., glacial acetic acid (22 mL) was added dropwise, causing foaming and formation of a precipitate. The contents were stirred overnight and filtered to afford the 2-amino-5-trifluoromethoxybenzoic acid as an amber solid (12.5 g, 87%). A small amount was recrystallized from ethyl acetate-hexanes to afford amber needles for an analytical sample and the remaining compound was used without further purification: mp 142.5-144.2 C. 1 H NMR (CDCl3, 300 MHz) 7.98 (s, 1H), 7.18 (d, 1H, J=8.0 Hz) 6.62 (d, 1H, J=8.0 Hz), 6.40 (brs, 2H). Anal. Calc’d for C8 H6 NO3 F3: C, 43.45; H, 2.73; N, 6.33. Found: C, 43.40; H, 2.65; N, 6.35.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; G.D. Searle & Co.; US6077850; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem