Month: June 2021

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. 153171-22-3, name is 2-(4-Bromobenzyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 153171-22-3

N-(4-Phthalimidomethyl)phenyl isatin A solution of 1.863 g (12.66 mmol) of isatin in 80 ml of anhydrous N,N-dimethylformamide (DMF) was treated at room temperature with 0.608 g (15.19 mmol) of sodium hydride (60% dispersion) for about 40 minutes until the formation of the hydrogen bubble ceased. Then, cuprous iodide (CuI, 5.303 g, 27.85 mmol) and 4-phthalimidomethyl bromobenzene (6 g, 18.99 mmol) were added; the reaction was allowed to stir under nitrogen at 160 C. for 16 hours. The reaction was cooled down to room temperature and mixed with 400 ml of chloroform. The resulting mixture was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was separated on a silica flash column (5 to 20% ether/toluene) to give the desired product in 1.76 g (36.4% yield). Rf: 0.2 (silica gel, 10% ether/toluene). MS (MALDI-TOF): m/z 384.437 (observed).

The synthetic route of 153171-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Corporation; US6165800; (2000); A;,
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Electric Literature of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0C. NaH (38 mg, 0.94 mmol, 60 wt.% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified silica chromatography, eluting with 0-20% EtOAc in hexanes. Desired fractions were concentrated in vacuo to afford the title compound, 1-23. LRMS (ESI) calc’d for Ci0H8BrF3NO [M+H]+: 294, found: 294.

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; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); 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. 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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Indoline | C8H9N – PubChem

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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Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
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;,
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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;,
Indoline – Wikipedia,
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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