Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-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 868066-91-5, Recommanded Product: 5-Bromo-2-methylisoindolin-1-one

General procedure: 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 solution of 2 M Na2CO3 (3 mL) and Pd(dppf)C12 (94 mg, 0.12 mmol) were added and the entire mixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30 mmol) was added and reflux continued under N2 overnight. Upon cooling, themixture was diluted with water (100 mL) and extracted with CH2C12 (6×50 mL). The combined organic fractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to give a crude solid which was purified by flash column chromatography on silica gel (EtOAc as eluant). The title compound was isolated as a light-brown solid (510 mg, 97percent). ?H NMR [400 MHz, (CD3)2S0] 8 7.87 (s, 1 H), 7.77 (dd, J? 7.9, 1.6 Hz,1 H), 7.67 (dd, J 7.9, 0.3 Hz, 1 H), 7.61-7.66 (m, 2 H), 7.18 (dd, J 5.0, 1.4 Hz, 1 H),4.49 (s, 2 H), 3.08 (s, 3 H). LRMS (APCI) calcd for C13H,2NOS 230 (MH), found 230.

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Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-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 7699-18-5, SDS of cas: 7699-18-5

General procedure: 4.4.2 (Z)-5-methoxy-3-((2-(4-methoxyphenyl)-1H-benzo[d]imidazol-6-yl)methylene)indolin-2-one (5b) Compound 5b was prepared according to the method described for compound 5a, employing aldehyde 11a (126 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81 mg, 0.5 mmol) to obtain the pure product 5c as a yellow solid (114 mg, 58%); mp: 177-179 C; IR (KBr): 3422, 3153, 2931, 2352, 1681, 1642, 1576, 1474, 1435, 1254, 1179, 1029, 961, 864 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.41 (bs, 1H), 8.25-8.16 (m, 3H), 7.82 (s, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.58 (d, J = 8.3 Hz, 1H), 7.40 (s, 1H), 7.12 (d, J = 8.6 Hz, 2H), 6.82-6.70 (m, 2H), 3.90 (s, 3H), 3.68 (s, 3H); 13C NMR (75 MHz, DMSO-d6): delta 168.9, 160.6, 154.3, 153.7, 153.1, 137.4, 136.2, 128.0, 127.9, 127.6, 126.1, 124.5, 123.7, 122.0, 121.9, 113.9, 109.9, 108.5, 55.0; MS (ESI): m/z 398 [M + H]+; HRMS (ESI): calcd for C24H20O3N3 m/z 398.14923 [M + H]+; found 398.14992.

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; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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Synthetic Route of 24566-79-8, A common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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: A mixture of the corresponding secondary amine 3a-d [23] (5.5mmol), anhydrous K2CO3 (6mmol) and compounds 2a-d (5mmol) were added in CH3CN (20ml). The mixture was heated at 65C for 8-10h. The solvent was evaporated under reduced pressure. Then water (25mL) was added, and the mixture was extracted with dichloromethane (20mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated under vacuum. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to obtain the oil products 4-7.

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; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 307 – 323;,
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Indoline | C8H9N – PubChem

Reference 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 oven dried flask containing an appropriate dicarbonyl compound 15 (isatin or acenaphthoquinone or ninhydrin, 0.5 mmol), an appropriate alpha-amino acid 16 (sarcosine or l-proline, 0.6 mmol) and an appropriate dipolarophile 6 (0.5 or 1 mmol) in an appropriate dry solvent (3-4 mL) was heated to the temperature and time as shown in the respective Tables/Schemes. Then, the reaction mixture was cooled to rt and the solvent was evaporated in vacuo, which afforded a crude reaction mixture. Then, the crude mixture was subjected to the silica gel column chromatography purification (EtOAc/hexane), which gave the corresponding spiro-pyrrolidine/pyrrolizidines containing heteroaryl moieties 17/18/19 (see the corresponding Tables/Schemes for specific entries).

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; Rajkumar, Vadla; Babu, Srinivasarao Arulananda; Padmavathi, Rayavarapu; Tetrahedron; vol. 72; 36; (2016); p. 5578 – 5594;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Bromomethylphtalimide (85 mg, 0.35 mmol), sodium iodide (53 mg, 0.56 mmol) and cesium carbonate (177 mg, 0.54 mmol) were added to a solution of DO3AtBu under argon atmosphere (172 mg, 0.33 mmol) in freshly distilled acetonitrile (5 mL). The suspension was heated to reflux for 24 h, before being filtered at room temperature. The yellow filtrate was evaporated under reduced pressure and 10 mL chloroform was added in order to precipitate residual inorganic impurities. Evaporation of the solvent and addition of 20 mL of ether led to precipitation of a yellow powder corresponding to the sodium adduct C35H55N5O8.NaI.H2O (191 mg, 67% yield). 1H NMR (CDCl3) d: 7.82-7.71 (m, 4H), 4.66 (s, 2H), 3.27-2,34 (broad signals overlapping, 22H), 1.48-1,40 (two signals overlapping, 27H); 13C NMR (CDCl3) d: 173.91, 173.30, 169.70, 134.58, 131.69, 123.59, 83.03, 82.73, 57.62, 56.48, 55.69, 53.55, 51.77, 51.15, 48.34, 28.06, 27.88. Anal. Calcd for C35H55N5O8.NaI.H2O: C, 49.94; H, 6.83; N, 8.32. Found: C, 50.13; H, 6.67; N, 8.49.

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

Reference:
Article; De La Reberdiere, Arnaud; Lachaud, Fabien; Chuburu, Francoise; Cadiou, Cyril; Lemercier, Gilles; Tetrahedron Letters; vol. 53; 45; (2012); p. 6115 – 6118,4;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The synthetic route of 2-(Bromomethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Indoline | C8H9N – PubChem

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. 3485-84-5, name is N-Vinylphthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: N-Vinylphthalimide

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (17 mg, 0.08 mmol), acetonitrile (50 mL), vV-vinylphthalimide (716 mg, 4.13 EPO mmol), triethylamine (1.6 niL, 11 mmol), tri-o-tolylphosphine (69 mg, 0.22 nimol) and 1- {3-[8-bromo-2-(2-methoxyethyl)-lH’-imidazo[4,5-c]quinolin-l-yl]propyl}pyrrolidin-2-one (1.62 g, 3.76 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 1200C in an oil bath for 15 hours. The reaction was cooled to ambient temperature and methanol (50 niL) and chloroform (50 ml) were added. After filtering through a 0.2 micron PTFE membrane, the solution was concentrated under reduced pressure and then purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-8% gradient of methanol in dichloromethane) to provide 2.0 g of2-(2-{2-(2-methoxyethyl)-l-[3-(2-oxopyrrolidin-l-yl)propyl]-lH-imidazo[4,5- c]quinolin-8-yl}ethenyl)-lH-isoindole-l,3(2H)-dione as a bright yellow solid. MS (APCI) m/z 524 (M + H)+.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2006/91394; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0, These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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: Indole (0.234 g, 2 mmol) and isatin (0.147 g, 1 mmol) were mixed in oxalic acid: proline (5 ml) as solvent and the resultant mixture was stirred at room temperature for appropriate time. After the completion of the reaction indicated by TLC, 5 ml distilled water was added. The insoluble crude product was filtered, washed with distilled water and recrystallized from ethanol.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chandam, Dattatray; Mulik, Abhijeet; Patil, Prasad; Jagdale, Suryabala; Patil, Dayanand; Sankpal, Sandeep; Deshmukh, Madhukar; Journal of Molecular Liquids; vol. 207; (2015); p. 14 – 20;,
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Synthetic Route of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2-oxoindoline-6-carboxylic acid (1.2 g, 6.77 mmol, 1.00 equiv), sulfuric acid (98%, catalytic amount) in CD3OD (50 mL) was stirred for 24 hours at 60 C. The reaction mixture was cooled to room temperature and the filtrate was concentrated under vacuum and poured into ice water. The pH was adjusted to 8 with NaHCO3 and the aqueous solution was extracted with ethyl acetate. The ethyl acetate was concentrated and the residue applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5) to give the title product 1.0 g (75%) as a brown solid. 1H NMR (400 MHz, CDCl3) delta: 10.54 (s, 1H), 10.50 (s, 1H), 7.58 (m, 1H), 7.34 (d, J=7.8 Hz, 2H), 3.45 (s, 2H).

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-Oxoindoline-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); 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. 15861-23-1, name is Indoline-5-carbonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8N2

To a solution of 5-cyanoindoline (0.5 g, 3.47 mmol) and the compound of Part D (1.3 g, 1.1 eq.) in 10 mL of DMF was added sodium hydride (60% in oil, 0.15 g, 1.1 eq.). The mixture was stirred overnight at rt. The reaction was diluted with water and extracted 3¡Á with EtOAc. The combined extracts were washed with water and brine and then dried over Na2SO4, filtered and evaporated. Flash chromatography on silica gel (hexane/CH2Cl2/EtOH 20/80/0.5) provided the desired alkylated product (0.44 g, 31%, MS m/z 414.2 (M+H)+) along with 68% of unreacted starting material.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem