Month: June 2021

These common heterocyclic compound, 17826-05-0, name is 5,6-Dibromoindoline-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. Application In Synthesis of 5,6-Dibromoindoline-2,3-dione

General procedure: Water (15 mL) was added to a mixture of 1.0 mmol of isatin derivative, 1.2 mmol of creatinine (for 2p, 2.3 mmol of creatinine) and 1 mol% of HAuCl4 and the resulting suspension was heated to reflux for 30 min. The clear reaction mixture was cooled to 15-20 C. The precipitated aldol product was filtered and washed with copious amount of water and then with methanol and ethyl acetate (EtOAc). The obtained product was thoroughly dried under vacuum to afford the pure product 2a-2p.

The synthetic route of 5,6-Dibromoindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Parthasarathy; Ponpandian; Praveen; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 38; 5; (2017); p. 775 – 783;,
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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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Computed Properties of C8H4ClNO2

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 °C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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Electric Literature of 205383-87-5, 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. 205383-87-5 name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, 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.

Step A: tert-butyl 5 -chloro-2-oxospiro [indoline-3 ,3 ?-pyrrolidinel- 1 ?-carboxylateTo a stirred solution tert-butyl 2-oxospiro[indoline-3,3?-pyrrolidine]-i?-carboxylate (800 mg,2.77 mmol) in dichioromethane (40 mL) and DMF (4 mL) was added N-chlorosuccinimide and the mixture was allowed to stir at room temperature overnight. Aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by ISCO (40g, EtOAc/Hex= 1 / 1) to give tert-butyl 5 -chloro-2-oxospiro [indoline-3 ,3 ?-pyrrolidine]- 1 ?-carboxylate. [M+ 1] =324.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Yeon-Hee; GUO, Zhuyan; ALI, Amjad; EDMONDSON, Scott, D.; LIU, Weiguo; GALLO-ETIENNE, Gioconda, V.; WU, Heping; GAO, Ying-Duo; STAMFORD, Andrew, M.; YU, Younong; KEVIN, Nancy, J.; ANAND, Rajan; SHA, Deyou; NEELAMKAVIL, Santhosh, F.; HUSSAIN, Zahid; KUMAR, Puneet; MONINGKA, Remond; DUFFY, Joseph, L.; XU, Jiayi; JIANG, Yu; SONE, Hiroki; CHAKRABARTI, Anjan; (183 pag.)WO2015/164308; (2015); A1;,
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Application of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

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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Related Products 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.

5-(Bromo)-1,3-dihydro-indol-2-one. A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to room temperature (RT) and stirred for 1 hour. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96%) as an off-white solid which was used without further purification: mp. 221-223 C.; 1H NMR (DMSO-d6) delta 3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) delta 36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-2-one, its application will become more common.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-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.

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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Application of 1127-59-9, The chemical industry reduces the impact on the environment during synthesis 1127-59-9, name is 7-Methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C ? H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60°C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Wei-Hong; Chen, Meng-Nan; Hao, Yi; Jiang, Xin; Zhou, Xiao-Lin; Zhang, Zhan-Hui; Journal of Molecular Liquids; vol. 278; (2019); p. 124 – 129;,
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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. 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, A new synthetic method of this compound is introduced below., SDS of cas: 88150-75-8

Example 8a synthetic process of amlodipine besylate,The difference from Embodiment 1 is thatStep three is: in the reaction tank,Into a toluene solution of 4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate,Distilled under reduced pressure at 70 C,Fill the water separator and continue to reflux under reduced pressure.Until the water content in the reflux liquid is ?0.2%, the temperature is lowered to 35 C, 27 kg of 2-chlorobenzaldehyde is added, and the internal temperature is maintained at 35 C.Add 1.5 kg of hexahydropyridine and stir for 30 minutes.Under the condition of 65 C, -0.09 Mpa, the water was refluxed under reduced pressure for 12 hours or more, the temperature was lowered to 35 C, and 120 kg of water was added.Stir,Let stand for 30 minutes,Layered, the lower aqueous layer is recovered, and the upper layer is a toluene solution of 2-(2-chloroindol)-4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate; The yield of amlodipine was 91.2%, and the purity was 99.5%.

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; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Liu Lijuan; Gao Huanhuan; Yu Yaoying; (13 pag.)CN108456160; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

41910-64-9, name is 4-Chloroindoline, 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. Quality Control of 4-Chloroindoline

A mixture of 4-chloroindoline (2.88 g) and D-glucose (3.38 g) in ethyl alcohol (150 ml)-H2O (10 ml) was refluxed under argon atmosphere overnight. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0-88:12) to give 4-chloro-1-(beta-D-glucopyranosyl)indoline (3.35 g) as a colorless foam. APCI-Mass m/Z 316/318 (M+H). 1H-NMR (DMSO-d6) delta 2.87-3.02 (m, 2H), 3.07-3.12 (m, 1H), 3.20-3.32 (m, 2H), 3.38-3.47 (m, 2H), 3.51-3.60 (m, 2H), 3.68-3.73 (m, 1H), 4.34-4.37 (m, 1H), 4.63 (d, J=8.3-Hz, 1H), 4.93 (d, J=5.1 Hz, 1H), 5.03 (d, J=4.0 Hz, 1H), 5.06 (d, J=4.5 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 6.60 (d, J=8.0 Hz, 1H), 6.99 (t, J=7.9 Hz, 1H).

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanabe Seiyaku Co., Ltd.; US2008/27122; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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. Safety of 6-(Trifluoromethoxy)indoline

HATU (2.10 g, 5.52 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (747 mg, 3.68 mmol), 2-((3-(2-(terf-butoxy)ethoxy)-5-methoxy- phenyl)amino)-2-(4-chlorophenyl)acetic acid 3c (1 .5 g, 3.68 mmol) and diisopropylethylamine (1 .82 mL, 1 1 .03 mmol) in DMF (30 mL). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification was carried out by flash chromatography on silica gel (15-40 muiotatauiota, 40 g, heptane/EtOAc 85/15). The pure fractions were combined and evaporated to dryness to give 2-((3-(2-(fe/t-butoxy)ethoxy)-5-methoxyphenyl)amino)-2-(4-chloro- phenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 3d (1 .33 g).

The synthetic route of 6-(Trifluoromethoxy)indoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (76 pag.)WO2017/167953; (2017); A1;,
Indoline – Wikipedia,
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