Tag: M.W=100-200

A common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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. 32372-82-0.

1-Ethyl-3- (3-dimethylaminopropyl)carbodiimide (1.63 g, 8.54 mmol, 2.0 eq.) was added to a stirred solution of S14 (950 mg, 4.27 mmol, 1 eq.), isoindoline hydrochloride (731 mg, 4.70 mmol, 1.1 eq.), 1-hydroxybenzotriazole (635 mg, 4.70 mmol, 1.1 eq.) N-,N-diisopropylethylamine (3.26 mL, 18.8 mmol, 4.4 eq.) in dichloromethane 42 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (30 mL). The organic layer was washed with 1 M hydrochloric acid solution (30 mL) and saturated sodium chloride solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Si02, 3 : 10 hexanes/ethylacetate) to afford S15 (1.22 g, 91.8%) as a white amorphous solid. 1H NMR (400 MHz, CDC13) delta 10.47 (s, 1H), 7.48 – 7.21 (m, 5H), 7.15 (d, J= 7.4 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 4.02 – 3.76 (m, 4H), 1.32 (d, J= 6.8 Hz, 7H).13C NMR (100 MHz, CDC13) delta 190.8, 167.6, 153.7, 144.9, 136.4, 136.4, 134.4, 132.5, 128.0, 127.7, 126.1, 123.3, 122.7, 111.2, 56.1, 53.4, 52.3, 27.3, 24.4 (2). HRMS (ESI+) m/z [M + Na+] calcd for C20H21NO3Na, 346.1419, found 346.1404.

The synthetic route of Isoindoline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3484-35-3

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 65 mg (42%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.30 (s, br, 1 H, NH-1′), 12.05 (s, br, 1 H, COOH), 10.67 (s, br, 1 H, NH-1), 7.57 (s, 2 H, H-vinyl, H-4), 7.12 (d, J=2.65 Hz, 1 H, H-2′), 6.91 (d, J=7.82 Hz, 1 H, H-6), 6.74 (d, J=7.82 Hz, 1 H, H-7), 2.65 (t, J=6.94 Hz, 2 H, CH2CH2COOH), 2.46 (t, J=6.94 Hz, 2 H, CH2CH2COOH), 2.30 (s, 3 H, CH3), 2.25 (s, 3 H, CH3); MS m/z (relative intensity, %) 311 ([M+1]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3484-35-3, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1914-02-9, name is 3,3-Dimethylindoline, 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 1914-02-9, 1914-02-9

To a solution of (R)-2-((tert-butoxycarbonyl)amino)propanoic acid (141 mg, 0.745 mmol) in 7 mL DMF, triethylamine (125 mu,, 0.897 mmol) and HATU (322 mg, 0.847 mmol) were added. After stirring at room temperature for 5 min, 3,3-dimethylindoline (101 mg, 0.686 mmol) was added. After stirring at room temperature for overnight, the mixture was extracted with AcOEt and brine. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give (R)-tert-butyl (l-(3,3-dimethylindolin-l-yl)-l-oxopropan-2- yl)carbamate (205 mg) as a white solid. LCMS m/z = 319.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 1.358 (s, 3H), 1.364 (s, 3H), 1.40 (d, J = 6.8 Hz, 3H), 1.45 (s, 9H), 3.78 (d, J = 10.0 Hz, 1H), 4.00 (d, J = 10.0 Hz, 1H), 4.54-4.61 (m, 1H), 5.46 (d, J = 8.5, 1H), 7.07-7.10 (m, 1H), 7.15-7.16 (m, 1H), 7.20-7.24 (m, 1H), 8.17 (d, J = 8.1 Hz, 1H).

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, 3,3-Dimethylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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. 2913-97-5.

A solution of the product of Example 3E (36.81 g) in methanol (50 mL) was treated with L-iso-leucine tert-butyl ester hydrochloride (30 g, 134 mmol), sodium cyanoborohydride (16.9 g, 268 mmol), and acetic acid (4.6 ml, 80.4 mmol), stirred at 25¡ã C. for 3 hours and concentrated. The concentrate was partitioned between dichloromethane and saturated NaHCO3. The organic phase phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with a gradient starting with 10percent-066percent ethyl acetate in hexanes to give the title compound (28.44 g, 59percent yield).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 603-62-3, name is 3-Nitrophthalimide, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 603-62-3

3-NITROPHTHALIMIDE (LOOGR) was taken into a hydrogenation kettle and dissolved using 500ML of dimethylformamide. 5% Palladium/carbon (LOGR, 50% wet) was added to the solution and subjected to hydrogenation conditions 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 hydrogen uptake was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent 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 3- aminophthalimide. Melting point: 263-4C.

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, 603-62-3, other downstream synthetic routes, hurry up and to see.

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

Adding some certain compound to certain chemical reactions, such as: 17630-75-0, name is 5-Chloro-2-oxindole, 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 17630-75-0. 17630-75-0

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

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 5-Chloro-2-oxindole.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 52351-75-4 name is 6-Methoxyindoline-2,3-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. 52351-75-4

A mixture of NaH (11.3 mmol, 2.0 eq) and ylide salt (11.3 mmol, 2.0 eq) was stirred at 0 C for 1h under N2 protection. Then 6-methoxyindoline-2,3-dione (5.6 mmol, 1.0 eq) was added and the mixture was stirred under 80 C for 2h. The resulting solution was poured into satd.aq. NH4Cl, and the organic layer was separated and dried over Na2SO4. The solvent was removed under reduced pressure and the product was dissolved in CH3CN, follwed by DMAP (11.3 mmol, 2.0 eq), (Boc)2O (11.3 mmol, 2.0eq) were added, the mixture was stirred under room temperature for 20 min. The crude product product was also obtained after the solvent was removed under reduced pressure and then dissloved in EA and stirred with Pd/C (20% w/w) under H2 condition for 4h under room temperature. The mixture was filtered and purified by silica gel chromatography (petroleum ether/ethyl acetate = 8/1-5/1) to afford the product 1t.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Methoxyindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Jin, Qiaowen; Zheng, Changwu; Zhao, Gang; Zou, Gang; Tetrahedron; vol. 74; 30; (2018); p. 4134 – 4144;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

14192-26-8, A common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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 the suspension of methyl 2-oxoindoline-6-carboxylate (50 gm, 0.261 mol) in IPA (350 ml) was added slowly SMO-powder (33.8 gm, 0.626 mol) and stirred for about 15 min. Benzyl chloride (44 g, 0.313 mol) was added after completion of the reaction at a reaction temperature of -5 to -10C for about 5hrs. The reaction mixture was quenched into ice-water (700 ml) and acidified with Cone. HC1 (2.0-2.5 ml). Filtered the reaction mixture, washed with water (2X100 ml) and dried the precipitate to obtain crude product which can be recrystallized from acetonitrile (28 ml) to obtain methyl-3-(hydroxy(phenyl)methylene)-2- oxoindoline-6-carboxylate pure crystalline solid (32 gm) (61%) (HPLC purity >97%). The filtrate was evaporated in vacuum to give unreacted methyl 2-oxoindoline-6-carboxylate. MR: 216-223C; IR (KBr, cm”1): 3178, 1711, 1651; 1H-NMR (400 MHz, DMSO): delta 3.80 (s, 3H), 7.17 (s, 1H), 7.28-7.31 (m, 2H), 7.46-7.50 (m, 3H), 7.72 (d, 2H, J = 6.0 Hz), 9.52 (s, 1H), 11.53 (s, 1H); 13C-NMR (100 MHz, DMSO): delta 22.12, 52.41, 101.13, 111.13, 119.23, 123.06, 126.65, 127.06, 128.65, 129.21, 132.26, 134.47, 136.99, 166.58, 172.52 and 175.80; MS: m/z 294 [M]”1

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; ARAVA, Veera Reddy; GOGIREDDY, Surendra Reddy; JASTI, Venkateswarlu; (45 pag.)WO2016/178064; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, A common compound: 496-12-8, name is Isoindoline, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A 1.0 g (8.4 mmol) amount of isoindoline was dissolved in 25 mL of acetonitrile. After addition of potassium carbonate (2.3 g ,16.8 mmol), the resulting mixture was heated at 70 C. After 30 min, the solution was allowed to cool to room temperature. A 4.2 mL (47.2 mmol) amount of 1-bromo-3-chloropropane was added and the reaction mixture stirred at room temperature for 24 h. The solvent was removed under reduced pressure and 60 mL water added to the residue. The product was extracted with 3×30 mL dichloromethane. The combined organic fractions were washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure. Purification by column chromatography (DCM:MeOH(NH3), 99:1 (v/v)) was performed and enabled collection of the product as a brown liquid (1.27 g,77%). TLC: Rf 0.7 (DCM:MeOH(NH3), 9:1, v/v). 1H NMR (300 MHz,CDCl3) delta: 7.21 (s, 4H, Haro); 3.95 (s, 4H, 2 CH2); 3.69 (t, J 6.8 Hz, 2H,CH2); 2.90 (t, J 7.1 Hz, 2H, CH2); 2.07 (p, J 7.0 Hz, 2H, CH2). 13C NMR (75 MHz, CDCl3) delta: 140.0 (2 Caro); 126.7 (2 Caro); 122.3 (2 Caro); 59.1 (2 CH2); 53.0 (CH2); 43.1 (CH2); 31.9 (CH2). LCMS (ESI+): Calc.for [M+H]: 196.05; 198.07. Found: 195.95; 197.91.

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Donnier-Marechal, Marion; Larchanche, Paul-Emmanuel; Le Broc, Delphine; Furman, Christophe; Carato, Pascal; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 89; (2015); p. 198 – 206;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

774-47-0, 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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

The synthetic route of 5,6-Difluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem