Category: indolines-derivatives

Related Products of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added to a solution of 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) in tetrahydrofuran(5mL) under argon atmosphere, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6):delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1535610; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7223-50-9, name is N-Propargylphthalimide, 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 7223-50-9, Safety of N-Propargylphthalimide

General procedure: The starting alkyne 1 (0.5 mmol) and dodecane as internal standard(0.22 mmol, 50 muL) were added to a suspension of the Cu-Pd-NPs/MCM-48 catalyst (10 mg) in toluene (5 mL). All reactions werecarried out in a Schlenk-type flask, fitted with a reflux condenser andsealed with a rubber septum. The reaction flask was purged and filledwith H2 (1 atm) through a balloon connected to the flask by a needle,and then heated at 110 ¡ãC. Then, the reaction mixture was centrifugedand the supernatant removed. The solvent was evaporated invacuo, and the crude product was purified by flash column chromatography(silica gel, hexane/EtOAc). The recovered solid catalyst waswashed with toluene (3 ¡Á 2 mL), dried in an oven, calcined at 150 ¡ãC(4 h), and reduced in H2 atmosphere at 200 ¡ãC before its reuse. The following known compounds included in Table 2 were characterizedby comparison of their chromatographic and spectroscopic data (FTIR,1H NMR, 13C NMR, and MS) with those described in the literature.Styrene (2a)18Yield: 46 mg (0.44 mmol, 89percent); colorless liquid.IR (film): 3082, 3060, 3027, 1630, 1496, 1449, 992, 909, 777, 698 cm?1.1H NMR (300 MHz, CDCl3): delta = 7.35 (m, 2 H), 7.25 (m, 3 H), 6.7 (dd, J =10.8, 17.1 Hz, 1 H), 5.71 (d, J = 17.1 Hz, 1 H), 5.20 (d, J = 10.8 Hz, 1 H).13C NMR (75 MHz, CDCl3): delta = 137.5, 128.5, 127.7, 126.1, 136.9, 113.7.MS: m/z (percent) = 104 (100, [M+]), 103 (40), 78 (35), 77 (17), 51 (17).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Buxaderas, Eduardo; Volpe, Maria Alicia; Radivoy, Gabriel; Synthesis; vol. 51; 6; (2019); p. 1466 – 1472;,
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Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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 6941-75-9, name: 5-Bromoisoindoline-1,3-dione

Sodium borohydride (3.48 g, 92.0 mmol) was added to the solutionof 5-bromopthalamide (2.0 g, 8.8 mmol) in THF, and theresultant suspensionwas cooled to 10 C. Then, BF3.Et2O (12.7 mL,102.6 mmol) was added slowly and the reaction mixture wasrefluxed. After 24 h, the reaction mixture was allowed to cool to0 C and cold H2O (18 mL) was added. EtOAc (100 ml) was addedand the reaction mixture was made alkaline using 6.0 M aqueousNaOH. The organic layer was separated and concentrated using arotary evaporator. The residue was diluted with Et2O (50 mL) andacidified to pH 2. The aqueous layerwas separated, made alkaline topH 10 using 6.0 M aqueous NaOH and extracted with EtOAc(70 mL). The organic layer was separated, washed with brine(3 70 mL), dried (Na2SO4) and concentrated using rotary evaporatorto yied the 5-bromo-isoindoline (47). The residue was used infurther reactions without purification.

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Reference:
Article; Ojha, Ritu; Nepali, Kunal; Chen, Chun-Han; Chuang, Kuo-Hsiang; Wu, Tung-Yun; Lin, Tony Eight; Hsu, Kai-Cheng; Chao, Min-Wu; Lai, Mei-Jung; Lin, Mei-Hsiang; Huang, Han-Li; Chang, Chao-Di; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 190; (2020);,
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Reference of 1029691-06-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 2; (i?,5′)-2-(7-Bromo-l,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-isoindole-l,3-dione; In a 5 L flask is mixed (i?,5′)-2-(3-oxo-cyclopentyl)-isoindole-l,3-dione (295.3 g, 1.29 mol), 4-bromophenyl hydrazine-HCl (287.9 g, 1.29 mol) and glacial acetic acid (3 L) with mechanical stirring. The reaction is refluxed for 5 h, and then cooled to room temperature. The reaction is poured into water (4 L) with rapid stirring. The solid is collected by vacuum filtration, washed with water (4 L) and air-dried for 30 min. The solid is slurried with MeOH (700 mL), collected by vacuum filtration and rinsed with MeOH (100 mL). The gray solid is air dried for 2 h, then dried overnight in a 50 0C vacuum oven to obtain 414.67 g (84%) of the title compound as a dark solid. ES/MS m/z (7W1Br) 381/383 [M+H]+.

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, 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/140448; (2009); A1;,
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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. 912999-79-2, name is 5-Chloroisoindoline hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 912999-79-2

General procedure: A mixture of Intermediate J (200 mg, 0.66 mmol), Compound 146A, 3-(4-chlorophenyl)pyrrolidine, (143 mg, 0.79 mmol), HATEG (380 mg, 1 mmol), and DIPEA ( 258 mg, 2 mmol) in DMF (5 mL) was stirred at room temperature overnight. The mixture was diluted with EtOAc (50 mL), washed with brine (15 mL x 3), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with preparative HPLC give Compound 146B. LC-MS (ESI) m/z: 469 [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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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Synthetic Route of 3484-35-3, A common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
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Reference of 675109-26-9, A common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

6-Bromoisoindolin-1-one (636 mg, 3.10 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (930 mg, 3.70 mmol), and Pd(dppf)Cl2 (125 mg, 0.150 mmol) were added to a dry flask and placed under N2. Potassium acetate (900 mg, 9.20 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (DMF) (18 mL) was added and the reaction was heated at 80 C. overnight. The reaction mixture was evaporated to dryness and the resulting material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexane to yield 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (493 mg, 62%). ESI-MS m/z calc. 259.1, found 260.1 (M+1)+. Retention time 1.24 minutes.

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; HADIDA RUAH, SARA S.; Miller, Mark; Zhou, Jinglan; Bear, Brian; Grootenhuis, Peter; US2009/143381; (2009); A1;,
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Reference of 7699-18-5, A common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: The appropriate compound 2 (10 mmol) was dissolved inmethanol (100 mL) and treated with the equivalent of the appropriatealdehyde 1 and piperidine (1 mL). For compounds 39, 41 and42 the yield was much lower (5%), and an improvement (15-20%)was obtained by replacing piperidine with 33% NH4OHThe reaction mixture was refluxed for 5-10 h, except for compounds39-42 which required a longer reflux time (16-24 h; theprogress of the reaction was followed by TLC). The precipitate,formed on cooling, was collected by filtration.Compounds 39e41 were purified by column chromatographywith petroleum ether/acetone as the eluent. Most of the crudeproducts were crystallized from methanol, except 27 (acetone/petroleumether), 34, 43-48, 50-52 (ethanol) and 42, 49 (toluene). Inthe case of compound 10, the two E/Z isomers were isolated byfractional crystallization from methanol.

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; Morigi, Rita; Locatelli, Alessandra; Leoni, Alberto; Rambaldi, Mirella; Bortolozzi, Roberta; Mattiuzzo, Elena; Ronca, Roberto; Maccarinelli, Federica; Hamel, Ernest; Bai, Ruoli; Brancale, Andrea; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 166; (2019); p. 514 – 530;,
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Related Products of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 a stirred solution of 31 (0.300 g, 0.852 mmol) in THF (10 mL) was added isopropylmagnesium chloride (0.46 mL, 2M solution in THF, 0.920 mmol) at room temperature. After 1 h the reaction mixture was cooled to -20 C and a solution of 3-(1,3-dioxoisoindolin-2-yl)propanal (32) (0.144 g,0.709 mmol) in THF (3 mL) added. The resulting solution was warmed to room temperature, quenched with brine (20 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organics were dried (Na2SO4), filtered and concentrated to give 33 which was used without purification in the next step

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACUCELA INC.; WO2008/131368; (2008); A2;,
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Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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. Computed Properties of C10H7NO2

Using N-vinylphthalimide and diphenylphosphine oxide as raw materials, the reaction steps are as follows:(1) Add N-vinylphthalimide (0.069 g, 0.4 mmol) to the reaction flask, diphenylphosphine oxide (0.081 g, 0.4 mmol),tert-butyl nitrite (0.041 g, 0.4 mmol), silver nitrate (0.07g, 0.04 mmol), ethanol (2.5mL), 30C reaction;(2) TLC tracks the reaction until complete;(3) The crude product obtained after completion of the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to give the target product (yield 71%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3485-84-5, its application will become more common.

Reference:
Patent; Jiangsu Qiangsheng Function Chemical Co., Ltd.; Zou Jianping; Ying Zhiyao; Zhang Peizhi; Tao Zekun; Li Jianan; (19 pag.)CN107573378; (2018); A;,
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