Month: March 2021

Reference of 100510-65-4, A common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

b) N-(3,3-Dimethyl-2-oxo-2,3-dihydro-lH-indol-6-yl)-2-methyl-isonicotinamide To a suspension of 2-methylisonicotinic acid (175 mg, 1.28 mmol) in dry toluene (12.8 ml) was added SOCl2 (167 mg, 103 mu, 1.4 mmol) and dry DMF (9.33 mg, 9.89 mu, 128 muetaiotaomicron) under an argon atmosphere. The mixture was heated under reflux for 2 hours and the solvent was evaporated under reduced pressure. The residue was suspended in dry dichloromethane (3.51 ml) and a suspension of 6-amino-3,3-dimethylindolin-2-one (0.15 g, 851 muiotaetaomicron) and DIPEA (330 mg, 446 mu, 2.55 mmol) in dry dichloromethane (5ml) was added portionwise. The suspension was stirred under an argon atmosphere at room temperature for 16 hours, then diluted with dichloromethane, water and 1 M aqueous sodium carbonate solution. The aqueous phase was extracted with dichloromethane. The combined organic layers were washed with 1 M aqueous sodium carbonate solution, dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using dichloromethane/ methanol as eluent. The title compound was obtained as brown solid (99 mg). MS ESI (m z): 296.3 [(M+H)+]. 1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.38 (s, 2H), 8.64-8.62 (m, 1H), 7.71 (m, 1H), 7.64-7.62 (m, 1H), 7.49 (m, 1H), 7.31-7.23 (m, 2H), 2.57 (s, 3H), 1.24 (s, 6H).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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 24566-79-8, HPLC of Formula: C14H16BrNO2

To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassiun:i thioacetaLe (2.78 g, 34.3 mmoi) portion wise and stirred for 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 niL) and stirred for I h. The resultant precipitated was filtered, washed with waLer (100 mL) and dried in vacuo to afford 4-i as an of f-whiLe solid(5.8 g, 93.5%). LCMS: 306.20 (MHi).

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:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; SHIRUDE, Pravin S.; (258 pag.)WO2017/6282; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

PREPARATION 11 5-Acetyl-2-oxindole To 95 ml. of carbon disulfide was added 27 g. (0.202 mole) of aluminum chloride, followed by the dropwise addition of a solution of 3 ml. (0.042 mole) of acetyl chloride in 5 ml. of carbon disulfide, with stirring. Stirring was continued for 5 minutes and then 4.4 g. (0.033 mole) of 2-oxindole was added. The resulting mixture was heated under reflux for 4 hours and cooled. The carbon disulfide was removed by decantation and the residue was triturated under water and recovered by filtration. After drying, 3.2 g. of the title compound was obtained, m.p. 225-227 C.

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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4658037; (1987); A;,
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. 20870-78-4, name is 5-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromoindolin-2-one

To a solution of 5-Bromo-1,3-dihydro-indol-2-one (318 mg, 1.5 mmol) and Bis(pinacolato)diboron (420 mg, 1,65 mmol) in dioxane (15 mL) was added KOAc (516 mg, 5.25 mmol). The resulting mixture was degassed, treated with [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium methylene choloride complex (62 mg, 0.075 mmol), heated at 90 C. for 12 h and concentrated. The residue was dissolved in CH2Cl2 (100 mL), washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel eluding with 30% ethyl acetate/hexanes to afford 320 mg of Example 133a (82%). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.27 (s, 12H) 3.46 (s, 2H) 6.81 (d, J=7.72 Hz, 1H) 7.49 (m, 2H) 10.51 (s, 1H)) MS (ESI) m/z 260.2 (M+H)+, 276.8 (M+NH4)+

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Iyengar, Rajesh R.; Judd, Andrew S.; Zhao, Gang; Kym, Philip R.; Sham, Hing L.; Gu, Yugui; Liu, Gang; Liu, Mei; Zhao, Hongyu; Clark, Richard F.; Frevert, Ernst U.; Cool, Barbara L.; Zhang, Tianyuan; Keyes, Robert F.; Hansen, Todd M.; Xin, Zhili; US2005/38068; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. Computed Properties of C10H9NO2

To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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.

Example 30 5-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)thiophene-3-carboxylic acid; To a stirred mixture at 0 C. of 2-(3-hydroxy-propyl)-isoindole-1,3-dione (0.2 g, 0.97 mmol), 0.7 M sodium bromide (0.70 ml, 0.46 mmol), TEMPO (3.0 mg, 0.02 mmol) in dichloromethane (1 ml) was added dropwise a solution of bleach (2.1 ml, 4.9 mmol) and sodium hydrogen carbonate (117 mg, 1.4 mmol). The mixture was stirred at 0 C. for 2 hours after the addition was finished. The mixture was extracted with ethyl acetate (3*20 ml). The combined organic extracts were washed with 10% sodium thiosulphate (3*10 ml), brine (10 ml), dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was washed with ethyl acetate (2*1 ml) affording after drying 161 mg (81%) of 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde as a solid. 1H NMR (400 MHz, CDCl3) delta 9.82 (s, 1H), 7.85 (dd, 2H, J=5.6, 2.8 Hz), 7.73 (dd, 2H, J =5.6, 2.8 Hz), 4.04 (t, 2H, J=7.2 Hz), 2.89 (t, 2H, J=7.2 Hz).

The synthetic route of 883-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jeppesen, Lone; Andersen, Henrik Sune; Olsen, Ole Hvilsted; Judge, Luke Milburn; Holsworth, Daniel Dale; Bakir, Farid; Axe, Frank Urban; Ge, Yu; US2005/119332; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 112656-95-8, 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. 112656-95-8, name is 7-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

7′-Nitro-spiro[1,3-dioxolan-2,3′-indol]-2′(1’H)-one (1b) was obtained as grey powder with yield 64%, m.p. 207-208 C [Found C 50.78, H 3.55, N 11.79. C10H8N2O5 requires C 50.85, H 3.41, N 11.86%]; numax (KBr) 1119, 1322, 1346, 1465, 1528, 1630, 1762, 3219 cm-1; deltaH (400.1 MHz, DMSO-d6) 4.30-4.40 (4H, m, -O-(CH2)2-O-), 7.24 (1H, dd, J 7.2, 8.6, -CH-CH-CH-C-); 7.77 (1H, dd, J 0.6, 7.2, -CH-CH-CH-C-), 8.12 (1H, dd, J 1.0, 8.6, -CH-CH-CH-C-), 11.17 (1H, s, NH); deltaC (100.6 MHz, DMSO-d6) 66.4, 123.3, 126.9, 131.6; MS (EI, 70 eV): m/z (I, %): 236 (41, M+), 219 (96), 208 (46), 191 (100), 175 (22), 161 (20), 147 (29), 131 (11), 117 (58), 106 (12), 90 (29), 75 (26), 63 (30), 43 (19), 30 (60).

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, 7-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zaryanova, Ekaterina V.; Ignatov, Alexander A.; Lozynskaya, Nataly A.; Tetrahedron; vol. 73; 49; (2017); p. 6887 – 6893;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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. name: 2-(Chloromethyl)isoindoline-1,3-dione

Under a protective nitrogen atmosphere, sodium hydride (NaH, 48 mg, 1.2 mmol) is added into a solution of berbamine dihydrochloride (205 mg, 0.3 mmol) in N,N-dimethyl formamide (5 ml) at 0 C., after being stirred for 1 hour, 2-chloromethyl-isoindoline-1,3-dione (88 mg, 0.45 mmol) is added therein. The reaction solution is heated to 80 C. overnight. Then the reaction mixture is evaporated under vacuum, and purified by a preparative thin layer chromatography to give white or pale yellow compound (BS-BE-001) (11.5 mg, 5.0%). [0105] LC/MS m/z: M+1 768.3 100% (purity). [0106] 1H NMR (CDCl3) delta:7.887.865 (dd, 2H, J=6.0 Hz, 5.5 Hz), 7.747.732 (dd, 2H, J=5.5 Hz, 6.0 Hz), 7.264 (s, 1H), 7.0196.998 (dd, 1H, J=8.5 Hz, 8.0 Hz) , 6.9196.903 (d, 1H, J=7.5 Hz), 6.716.698 (d, 1H, J=7.5 Hz), 6.626.614 (m, 1H), 6.527 (s, 1H), 6.4206.385 (m, 1H), 6.266 (s, 1H), 5.954 (s, 1H), 5.7665.717 (m, 2H), 3.850 (s, 2H), 3.750 (s, 3H), 3.610 (s, 3H), 3.4873.473 (m, 1H), 3.396 (s, 1H), 3.2413.203 (m, 2H), 3.113 (s, 3H), 3.0122.768 (m, 6H), 2.566 (s, 3H), 2.532 (s, 1H), 2.3832.271 (m, 1H), 2.216 (s, 1H), 1.7951.725 (m, 2H).

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

Reference:
Patent; HANGZHOU BENSHENG PHARMACEUTICAL CO., LTD.; Xu, Rongzhen; Rong, Frank; Xie, Fuwen; Lai, Hongxi; US2013/158068; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 132898-96-5, 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. 132898-96-5 name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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.

Morpholine (1.1 mL, 12.2 mmol) was added to a solution of 2,3-diupsilonxoLndoline-5-sulfonyl chloride (3.0 g, 12.2 mmol) and diibopropylethyl amine (7,0 mL, 40 mmol) m 1 :1 CH2CWTHF ( 120 mL at -50 C. The solution was warmed to room temperature and stirred at that temperature for 12 hours. The reaction mixture was concentrated, then dissolved m CHjCl2. and washed with saturated NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, then concentrated, and purified by flash chromatography on silica gel (5% MeOH in CH:CU) to provide 2.4 g of the product

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dioxoindoline-5-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem