Tag: M.W=200-300

Synthetic Route of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: 1M solution of phenylmagnesium bromide in THF (20.40mL, 20.40mmol) was added dropwise to a stirred ice-cold solution of isatin (1g, 6.80mmol) in anhydrous THF (20mL) that was kept under nitrogen. The reaction was stirred at room temperature for 2h and then quenched with a saturated aqueous solution of NH4Cl (20mL). Water was then added (30mL) and the aqueous phase was extracted twice with dichloromethane (2¡Á60mL). The organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed in vacuum and the crude was purified by crystallization from EtOAc/Hexane to afford 1 (1.18g, 77.1%) as a white powder.

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; Denoyelle, Severine; Chen, Ting; Yang, Hongwei; Chen, Limo; Zhang, Yingzhen; Halperin, Jose A.; Aktas, Bertal H.; Chorev, Michael; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 537 – 553;,
Indoline – Wikipedia,
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Related Products of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A septum-capped vial with a stirring bar was charged with the corresponding isatin(0.1 mmol), ester (0.2 mmol, 2.0 equiv.), catalyst and solvent (1 mL). The reactionmixture was conducted in setting temperature and monitored by TLC. The resultingreaction mixture was vapored in vacuum and the residue was purified by columnchromatography (Hexane/EtOAc = 8/1 to 4/1). The desired products were obtained ascolorless oil or white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Zhang, Xianhui; Zhou, Li; Mahmood, Qaiser; Zhao, Mengmeng; Wang, Xiaowu; Wang, Qinggang; Synlett; vol. 30; 5; (2019); p. 573 – 576;,
Indoline – Wikipedia,
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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. 107583-37-9, name is 5,6,7-Trifluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,6,7-Trifluoroindoline-2,3-dione

EXAMPLE 6 5,7-difluoro-6-(4-methylpiperazinyl)isatin STR14 Using the procedure in Example 4 and substituting 5,6,7-trifluoroisatin for 5,6-difluoroisatin gave the title compound in 70% yield.

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; PathoGenesis Corporation; US5441955; (1995); A;,
Indoline – Wikipedia,
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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 3339-73-9

240 g (1.09 mol) of phthalic anhydride alanine was added to a 1000 mL reaction flask.700 mL of chloroform, warmed to 60 C, and 135 g (1.13 mol) of thionyl chloride was added dropwise.After the completion of the dropwise addition, the reaction was kept for 3 hours, and concentrated under reduced pressure to dryness.Add 400 mL of chloroform to dissolve and set aside.

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; Hubei Hongtai Biological Technology Co., Ltd.; Zhang Rui; Lei Yuping; Wang Liming; Wu Weiwei; Li Jianxiong; (8 pag.)CN109053580; (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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 885272-46-8

To a solution tert-butyl 4-bromoindoline-1-carboxylate (1.0 g, 3.354 mmol) and benzophenone hydrazone (0.658 g, 3.354 mmol) in 1,4-dioxane (15 mL) at room temperature under nitrogen, BINAP (209 mg, 0.335 mmol), palladium (II) acetate (75 mg, 0.335 mmol) and sodium t-butoxide (967 mg, 10.061 mmol) were added and the mixture was heated at 100 C. for 16 h. The resultant mixture was cooled to room temperature, filtered and the filtrate concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient). Pure fractions were combined and concentrated. The resultant solids were dried under reduce pressure to afford tert-butyl 4-(2-(diphenylmethylene)hydrazinyl)indoline-1-carboxylate, cpd 130a (912 mg, 65.8% yield). MS m/z 414.1 (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; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
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Application of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-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.

A mixture of 5-bromoisoindoline-1,3-dione (2.5 g, 11.06 mmol) and Pd(Ph3P)4 (1.406 g, 1.217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1.299 g, 11.06 mmol) was added, and the solution, splitted in 5 vials, was heated under microwave irradiation at 200 C. for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added, and the organic phase was extracted with ethyl acetate (3¡Á150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM_MeOH=99:1) to afford 1,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH]+).

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

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H6BrNO2

General procedure: A mixture of isatin 1 (1 mmol) and malononitrile (2) (1 mmol) in EtOH (3 mL) was stirred for 15 min then treated with a solution of dialkyl acetylenedicarboxylate 3 (1 mmol) and 3,4-dimethylaniline (1 mmol) in EtOH (1 mL). The mixture was stirred at room temperature for 8 h. After completion of the reaction (TLC, eluent: EtOAc/hexane, 1:2), the mixture was filtered and the precipitate washed with H2O (5 mL) and EtOH (5 mL) to afford the pure product 4.

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 2058-72-2.

Reference:
Article; Tisseh, Zeinab Noroozi; Ahmadi, Fereshteh; Dabiri, Minoo; Khavasi, Hamid Reza; Bazgir, Ayoob; Tetrahedron Letters; vol. 53; 28; (2012); p. 3603 – 3606;,
Indoline – Wikipedia,
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Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

General procedure: An equivalent mixture of aldehyde (1 mmol) and active methylene compound- barbituric acid/1, 3-dimethyl barbituric acid/ 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1 mmol) in dimethyl formamide (2 mL) was subjected to microwave irradiations at 150 C for 1 h. The reaction was monitored by TLC. After the completion, the reaction was quenched by adding water to the reaction mixture. The crude product was separated out as solid, which was further purified by washing with ethanol, hot water and recrystallization from chloroform:methanol (9:1).

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singh, Harpreet; Kaur, Manpreet; Kaur, Harpreet; Sharma, Indu; Bhandari, Anmol; Kaur, Gurcharan; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
Indoline – Wikipedia,
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. 3335-98-6, name is 1-Phenyloxindole, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H11NO

1-phenyl-2,3-dihydro-1H-indol-2-oneTo 100 g (0.48 mol) was added to 1.5 L CH2Cl2. It was added to phosphoryl chloride 267 mL (2.87mol) at room temperature and heated to reflux for 12 hours. Slowly added dropwise to the ice-water cooling, the reaction solution and the reaction was terminated. The organic layer was extracted with CH2Cl2 and 2.0 L sat. Neutralized with aqueous NaHCO3 solution and washed with distilled water. The resulting organic layer was dried over anhydrous MgSO4, and evaporated under reduced pressure and purified by silica gel column chromatography to give the title compound 40.3 g (yield 37%):

The synthetic route of 3335-98-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doosan Corporation; Sim, Jae Uii; Park, Sung Jin; Jang, Ji Sung; (28 pag.)KR2016/41676; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

169037-23-4, name is 5-(Trifluoromethoxy)indoline-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. Product Details of 169037-23-4

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(p-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5l): Melting point 270-272 C; White solid, 92%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.64 Hz, 1H), 4.67-4.70 (m, 1H), 4.33 (d, J = 10.24 Hz, 1H), 3.86 (d, J = 13.92 Hz, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.76 (d, J = 16.92 Hz, 1H), 3.47 (d, J = 15.4 Hz, 1H), 3.06 (d, J = 11.72 Hz, 1H), 2.75-2.79 (dd, J = 13.96, 8.08 Hz, 1H), 2.72 (d, J = 13.92 Hz, 1H), 6.59-6.66 (m, 2H), 7.14-7.63 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.6, 47.3, 52.7, 53.1, 55.3, 55.4, 61.1, 67.3, 70.9, 100.8, 109.7, 114.1, 114.4, 121.1, 122.2, 124.7, 124.9, 126.5, 127.4, 128.5, 128.6, 128.7, 129.3, 129.9, 130.1, 130.4, 134.5, 136.9, 138.3, 138.5, 138.7, 139.8, 139.8, 144.4, 179.6, 197.2. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.71; H, 5.34; N, 5.56.

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

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem