Tag: M.W=100-200

Electric Literature of 1504-06-9,Some common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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.

Step 2: Preparation of 3-methyl-3-(pyrimidin-5-ylmethyl)-l,3-dihydro-2H-indol-2-onePyrimidin-5-ylmethanol (510 mg, 4.63 mmol) in tetrahydrofuran (8 mL) at room temperature was treated with sodium hydride (185 mg, 4.63 mmol) and stirred for 5 minutes, p-Toluenesulfonyl chloride (883 mg, 4.63 mmol) was added, and the resulting mixture stirred for one hour to form pyrimidin-5-ylmethyl 4-methylbenzenesulfonate. In a separate flask 3- methyloxindole (682 mg, 4.63 mmol) and JV,iV-dimethylethylenediamine (1.538 mL, 10.19 mmol) in tetrahydrofuran (16 mL) were cooled to -78 0C and treated dropwise with n-butyllithium (2.5M in hexanes, 4.08 mL, 10.2 mmol). The mixture was allowed to warm to 0 0C and stirred for 15 minutes. The mixture was recooled to -78 C. To this mixture was added the tetrahydrofuran solution of pyrimidin-5-ylmethyl 4-methylbenzenesulfonate via cannula; the resulting reaction mixture was allowed to warm to room temperature and was stirred for 18 hours. Water (50 mL) was added, and the mixture extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/hexane to afford 3-methyl-3-(pyrimidin-5-ylmethyl)-l,3-dihydro-2H- indol-2-one as a white solid.1H NMR (CDCl3): delta 8.97 (s, 1 H), 8.29 (s, 2 H), 7.88 (br s, 1 H), 7.25 (d, 1 H, J = 7.3 Hz), 7.20 (m, 1 H), 7.1 1 (m, 1 H), 6.74 (d, 1 H, J = 7.8 Hz), 3.20 (d, 1 H, J – 13.5 Hz), 3.0 (d, 1 H, J – 13.5 Hz), 1.57 (s, 3H) MS: m/e 240.19 (M + H)+

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

Reference:
Patent; MERCK & CO., INC.; WO2009/45386; (2009); A1;,
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. 769965-95-9, name is 5′-Fluorospiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., SDS of cas: 769965-95-9

Example 2.5Trans-2-chloro-N-{-4-((5′-fluoro-2′-oxospiro[cyclopropane-1 ,3′-indoline]-1 yl)methyl)cyctohexyl}-5-(trifluoromethyl)benzamide 5′-Fluorospiro[cyclopropane-1 ,3′-indolin]-2′-one (Intermediate H) {67 mg, 0.378 mmol) in dry D F (3 ml) was treated with NaH {60% in mineral oil) (15.12 mg, 0.378 mmol) under N2 and the contents left stirring for ~10 mins. After this time, trans- methanesulfonic acid 4-{2-chloro-5-trifluoromethyl-benzoylamino)-cyclohexyl methyl ester (Intermediate C) (105 mg, 0.253 mmol) was added and the solution heated to 70C for 2.5 h. After cooling to RT overnight, the mixture was diluted with EtOAc/H20 (40 ml) and transferred to a separating funnel. The organic layer was separated and washed with brine, dried (MgS04), and concentrated in vacuo to give a light brown oil. The crude oil was chromatographed on silica eluting with a gradient of 0%-30% EtOAc/iso-hexane follwed by an isocratic gradient of 30% EtOAc/iso-hexane to afford the title compound as a white solid; LC-MS Rt= 1.36 mins; [M+H]+ 495.3; Method = 2minl_C_30_v002. 1H NMR (400 MHz, CDCI3). delta 7.90 (1H, s), 7.55 (1 H, d), 7.50 (1H, d), 6.95 (1H, m), 6.80 (1 H, m), 6.60 (1H, m), 5.95 (1 H, d), 4.0 (1H, m), 3.65 (2H, d), 2.20 (2H, m), 1.85 (5H, m), 1.55 (2H, m), 1.25 (4H, m).

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; ATKINSON Benjamin; BEATTIE David; CULSHAW Andrew James; DEVEREUX Nicholas James; MCKENNA Jeffrey; DALE James; WO2011/92293; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 one-neck round-bottom flask equipped with magnetic stirringwas added 6-chloro-2-indolinone (2a, 1.00 g, 6.0 mmol),vinamidinium salt 324 (2.02 g, 12.0 mmol), Et3N (1.82 g, 18.0mmol), and DMF (10 mL). The mixture was stirred for 20 h atr.t., after the reaction was complete (monitored by TLC,EtOAc/MeOH = 20:1), 30 mL EtOAc and 30 mL water was added,then the aqueous layer was extracted with 30 mL EtOAc. Thecombined EtOAc layer was washed with sat. NaCl solution (15mL) and water (15 mL) then dried over Na2SO4. After filteringthe desiccant, the solvent was concentrated under vacuum to avolume of about 5 mL. The mixture was titrated with 15 mL nhexaneto give a yellow precipitant, the solid was filtered, anddried under vacuum to give 4a (1.34 g, yield 88%), a yellowpowder, which was used in the next step without further purification;mp > 250 C.

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

Reference:
Article; Tian, Shaixiao; Mao, Yu; Jiang, Yongjun; Xu, Guangyu; Synlett; vol. 29; 7; (2018); p. 949 – 953;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-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 89-40-7, COA of Formula: C8H4N2O4

4-Nitrophthalimide (LOOGR) was taken into a hydrogenation kettle and dissolved using 700ML of dimethylformamide. 5% PALLADIUM/CARBON (LOGR, 50% wet) was added to the solution and hydrogenated initially at 20-30C under 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogenation was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Dimethylformamide was removed from the filtrate under reduced pressure at 60-80C. Water (500ML) was added to the residue and the mixture stirred for 30MIN. The product was isolated by filtration and dried at 60-70C to get 80gr (95%) of yellow crystalline solid of 4- aminophthalimide. Melting point: 294-5C.

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

Reference:
Patent; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 60434-13-1 as follows. HPLC of Formula: C9H6ClNO2

General procedure: To a stirred solution of isatin 6 (20 mmol) in dry DMF (30 mL), K2CO3 (30 mmol) wasadded and stirred for 10 min. 7 (24 mmol) was added dropwise to the reaction mixture. Thereaction mixture was then stirred at room temperature overnight. Ice water was added and theprecipitate produced which was collected by filtration. Orange solid 8 was obtained afterdried by vacuum. Solid 8 was then dissolved in NH2NH2H2O (20 mL) and the reaction mixture washeated to 130 oC. After 3 h, the reaction was cooled and diluted with EtOAc. The aqueouslayer was extracted with EtOAc. The combined organic layer was washed with saturatedaqueous NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated under reducedpressure. The residue 9 was used directly without purified. To a suspension of NaH in THF, N-substitued oxoindole 9 was added by portion in 0 oC.after stirred for 10 minutes, correspond isocyanate was added by potions. The mixture wascontinue stirred overnight. It was quenched by 1M HCl to adjust the PH to 2~5 and thendiluted with EtOAc. The water layer was extracted with EtOAc. The combined organic layerwas washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel. (PE/EA = 5/1) togive compound 1a-1r as a white solid.

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Hui; Liu, Hui; Zhao, Si-Han; Cheng, Shao-Bing; Xu, Xiao-Ying; Yuan, Wei-Cheng; Zhang, Xiao-Mei; Synlett; vol. 30; 9; (2019); p. 1067 – 1072;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20870-79-5, name is 5-Nitroindolin-2-one, 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 20870-79-5, Computed Properties of C8H6N2O3

To the mixture of 5-nitro-2-oxindole 2c (0.5g, 0.003mol) and zinc dust (0.91g, 0.014mol) in ethanol (5mL) 2mL of concentrated hydrochloric acid were rapidly added with intensive stirring. After 30min the reaction was terminated by addition of cold water (3mL). Then solid sodium bicarbonate was carefully added to the reaction mixture to adjust pH 8. Solvent was removed in vacuum and crude product was purified by filtering through silica gel pad (eluent MeOH:EtOAc 1:1). After eluent evaporation in vacuum the 5-amino-2-oxindole 2d was obtained as gray powder with yield 79% (0.35g) and used without additional purification. Mp (exp)=190-195C, mp lit34=212-214C). dH (400MHz, DMSO-d6): 3.31 (2H, s, CH2), 4.64, (1H, br s, NH2) 6.39 (1H, dd, J 8.1, 1.3, CHAr), 6.51 (1H, s, CHAr), 6.53 (1H, d, J 7.6, CHAr), 9.99 (1H, s, NH).

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; Lozinskaya, Natalia A.; Babkov, Denis A.; Zaryanova, Ekaterina V.; Bezsonova, Elena N.; Efremov, Alexander M.; Tsymlyakov, Michael D.; Anikina, Lada V.; Zakharyascheva, Olga Yu.; Borisov, Alexander V.; Perfilova, Valentina N.; Tyurenkov, Ivan N.; Proskurnina, Marina V.; Spasov, Alexander A.; Bioorganic and Medicinal Chemistry; vol. 27; 9; (2019); p. 1804 – 1817;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, category: indolines-derivatives

General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.

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; Shang, Jian-Li; Guo, Hui; Li, Zai-Shun; Ren, Biao; Li, Zheng-Ming; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 724 – 727;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 611-09-6 as follows. name: 5-Nitroindoline-2,3-dione

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

According to the analysis of related databases, 611-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, 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: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

Statistics shows that Isoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 480-91-1.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6,Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem