Tag: M.W=100-200

Reference of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, 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.

To a mixture of indoline-5-carboxylic acid (500 mg, 3.07 mmol) in DMF (3 mL) was added Pyridine (0.2 mL) at 0 C followed by acryloyl chloride (555 mg, 6.13 mmol). The reaction mixture was stirred at RT for 5 h. The mixture was then concentrated, DCM was added (20 mL), washed with 0.5N HC1 (10 mL), dried over Na2504, filted and concentrated in vacuo to afford 1- acryloylindoline-5-carboxylic acid (280 mg, 42%) as a yellow solid. [M+H] Calc?d for C12H11N03:218.1; Found: 218.1

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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. SDS of cas: 317-20-4

Potassium Hydroxide (1.58 g; 28.16 mmol; 3.1 eq.)was added portion wise to a solution of 7-Fluoro-1H-indole-2,3-dione(1.50 g; 9.08 mmol; 1.0 eq.) in acetone (1.0 mL; 13.63 mmol; 1.5 eq.), ethanol (4.50 mL) and water (1.50 mL) in a microwave tube. The reaction was placed in a microwave oven and heated at 100C for 20 min. The reaction mixture was concentrated under vacuum. Water was added followed by a 5N solution of hydrochloric acid until the pH of the solution reached 4. The suspension was then filtered and the solid obtained dried. 8-fluoro-2-methylquinoline-4-carboxylic acid (1.60 g; 85%) was isolated as a brown solid. MS(ES+) m/z 206 (MH+).

The synthetic route of 7-Fluoroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boiteau, Jean-Guy; Ouvry, Gilles; Arlabosse, Jean-Marie; Astri, Stephanie; Beillard, Audrey; Bhurruth-Alcor, Yushma; Bonnary, Laetitia; Bouix-Peter, Claire; Bouquet, Karine; Bourotte, Marilyne; Cardinaud, Isabelle; Comino, Catherine; Deprez, Benoit; Duvert, Denis; Feret, Angelique; Hacini-Rachinel, Feriel; Harris, Craig S.; Luzy, Anne-Pascale; Mathieu, Arnaud; Millois, Corinne; Orsini, Nicolas; Pascau, Jonathan; Pinto, Artur; Piwnica, David; Polge, Gaelle; Reitz, Arnaud; Reverse, Kevin; Rodeville, Nicolas; Rossio, Patricia; Spiesse, Delphine; Tabet, Samuel; Taquet, Nathalie; Tomas, Loic; Vial, Emmanuel; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 945 – 956;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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.

Under argon atmosphere, 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) was dissolved in tetrahydrofuran(5mL). A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added, 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. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by 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.; EP1514544; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 5-Nitroindoline 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;,
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Indoline | C8H9N – PubChem

Related Products of 20870-79-5, A common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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 the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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Indoline | C8H9N – PubChem

Electric Literature of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

In a 100 mL single-mouth bottle, dihydroindole-5-carboxylic acid methyl ester (800 mg, 4.50 mmol) was added and methanol was added.(15 mL) was dissolved, followed by the addition of potassium hydroxide (760 mg, 13.5 mmol), and reacted at 45 C for 15 h. After the reaction was completed,Dilute with 100 mL of water, then adjust the pH to 2 with 2M diluted hydrochloric acid, and use dichloromethane (50 mL×3).Drying and spinning off the solvent gave the title compound.

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

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Ge Chongxun; Huang Yiqiang; Cao Chen; Li Qingqing; Hou Shaohua; (63 pag.)CN108276382; (2018); A;,
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. 13220-46-7, name is 4-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Methylindolin-2-one

Example 83 (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one (S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 78f (40 mg, 0.12 mmol 1) and 4-methyl-1,3-dihydro-indol-2-one (18 mg, 0.12 mmol) were dissolved in 1.5 ml of ethanol, and added with 6 mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45 C. for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml*2) and dried to obtain the title compound (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 83 (35 mg, yield 63.6%) as a yellow solid.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

Alternatively the amino compounds of the present invention can be synthesized applying Weinreb-rype chemistry (Tetrahedron Letters 2000, 41(8): 1141). As an example, the commercially available isoindoline 2 can be coupled to a commercially available N-protected amino ester (e.g., N-(diphenylmethylene)glycine ethyl ester ) 5 to form the amide 6 by first treating the amine 2 with an organo aluminum species such as trimethyl aluminum and adding the resulting organometallic intermediate to the protected amino ester 5 in an appropriate solvent such as DCM. Treatment of 6 with benzylbromide in the presence of a phase transfer catalyst (e.g., tetrabutylammonium bromide, TBAB) and a suitable base (e.g., potassium hydroxide, KOH) and a solvent such as DCM yields 7, (Journal of the American Chemical Society, 1989, 111(6):2353), which upon treatment with an acid (e.g., HCl) in a suitable solvent such as DCM produces 8, a compound of the present invention; To a solution of isoindoline (690 mg, 5.79 mmol) in DCM (5 ml) is added a 2M solution of trimethyl aluminum in heptane (2.9 ml, 5.79 mmol) and the resulting solution is allowed to stir at ambient temperature for 30 minutes. To this solution is added a solution of (benzhydrylidene-amino)-acetic acid ethyl ester (1.29 g, 4.82 mmol) in DCM (5 ml). The reaction is allowed to stir at ambient temperature for 18 h and carefully quenched with a 10% aqueous solution of citric acid. The resulting biphasic mixture is diluted with DCM (10 ml) and extracted with a saturated solution of Rochelle’s Salt (10 ml). The organic layer is separated, concentrated in vacuo and purified by column chromatography (hexanes-ethyl acetate 7-70%) resulting in 2- (Benzhydrylidene-amino)-l-(l,3-dihydro-isoindol-2-yl)-ethanone (1.0 g, 61%). 2-(Benzhydrylidene- amino)-l-(l,3-dihydro-isoindol-2-yl)-ethanone is analyzed by HPLC/Mass Spec.

The chemical industry reduces the impact on the environment during synthesis Isoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

4.92 g (0.03 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 50 ml of dimethylformamide under nitrogen atmosphere and stirred at room temperature for about 10 minutes. Then, 5.3 g mol) and 6.1 ml (0.036 mol) of diisopropylethylamine (DIPEA) were successively added to the reaction mixture. The reaction solution was gradually heated and stirred at 70 C for 4 hours to complete the reaction. After cooling the reaction mixture to room temperature, 100 ml of distilled water and 200 ml of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was separated and washed with H 2 O. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure 7.41 g (97.2%) of 6-nitro-2,3-dihydro-1- (1-phenylmethyl) -1H-indole (73) as a yellowish liquid was obtained.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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 chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.19 (Z)-N-(4-Fluorophenyl)-2-(7-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (3-19) Yield 70percent; m.p.: 242-244 °C; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.89 (s, 1H, NNH), 11.33 (s, 1H, NH), 10.84 (s, 1H, SCNH), 7.68-7.66 (m, 2H, J = 8.0 Hz, Ar2-H3 and Ar2-H5), 7.61 (d, 1H J = 7.2 Hz, Ar1-H4), 7.49-7.48 (m, 2H, J = 4.4 Hz, Ar2-H2 and Ar2-H6), 7.20 (d, 1H J = 7.2 Hz, Ar1-H6), 7.03 (t, 1H J = 7.6 Hz, Ar1-H5), 2.24 (s, 3H, CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.3, 163.1, 141.1, 137.4, 132.9, 132.7, 130.0, 128.2, 127.2, 122.3, 120.5, 119.4, 118.8, 15.8; IR: (KBr, nu/cm-1), 3308 (NN-H), 3165 (CON-H), 3052 (Ar-H), 1695 (-CONH-), 1625 (C=N), 1572 and 1539 (Ar-C=C), 1209 (C=S), 1153 (N-N); Elemental analysis calculated for C16H13FN4OS, C: 58.52, H: 3.99, N: 17.06, found C: 58.75, H: 3.66, N: 17.45.

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; Zhang, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem