Tag: M.W=100-200

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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., name: 5-Bromoindoline

1,1-Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1-carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at room temperature. After 10 min, the mixture gradually became a suspension. After 3 hours, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and dried under house vacuum for 5 hours to give 1 ,1-Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1- carboxylate (ca. 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H),3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MEDINA, Jesus Raul; CHARNLEY, Adam Kenneth; ROMERIL, Stuart Paul; WO2015/56180; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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.

1,3-Dihydro-2H-indol-2-one (5.25 g, 39.43 mmol) (Aldrich) was treated with a 1:1 solution of glacial acetic acid and distilled water (246 mL). The resulting reaction mixture was cooled to 0 C and then slowly treated with N-bromosuccinimide (14.03 g, 78.85 mmol) (J.T. Baker). After the complete addition of N-bromosuccinimide, the cooling bath was removed, and the reaction mixture was stirred at 23 C for 1 h. Upon stirring at 23 C, the reaction mixture became viscous and a white solid precipitated. The reaction mixture was poured into 500 mL distilled water and filtered to provide a crude white solid. Recrystallization from methanol provided pure 5-bromo-1,3-dihydro-2H-indol-2-one as a light pink solid. (Yield 5.28 g, 63%; mp 219 – 220 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; F. HOFFMANN-LA ROCHE AG; EP1149092; (2003); B1;,
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 341988-36-1 as follows. Formula: C10H11NO2

To a solution of methyl indoline-6-carboxylate (600 mg, 3.40 mmol),1-(3-bromo-l-methyl- 6,7-dihydro-1N-pyrazolo[4,3-clpyridin-5(4H)-yl)ethanone (Intermediate B, 960 mg, 3.74 mmol), 2-dicyclohexylphosphino-2? ,6? -di-i-propoxy- I , 1? -biphenyl (158 mg, 0.34 mmol) andchloro(2-dicyclohexylphosphino-2?,6? -di-i-propoxy- 1,1? -biphenyl) [2-(2- aminoethylphenyl)]palladium(1l), methyl-tert-butylether adduct (277 mg, 0.34 mmol) in dioxane (10 mE) was added e-BuONa (976 mg, 10.20 mmol). The mixture was heated to 120°C for 16 h under a nitrogen atmosphere. After cooling the reaction to room temperature, water (20 mL) was added and the mixture was extracted with EtOAc (20 mE x 2). 1 M HC1(2 mL) was added to aqueous phase and then extracted with EtOAc (20 mL x 2), The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by reverse phase chromatography (acetonitrile 5-35percent / 0.1percent NH4HCO3 in water) to give the title compound (120 mg, 10percent) as a brown solid. ?HNMR (400 MHz, DMSO-d6) oe 7.58 (s, IH), 7.28 (d, J= 7.2 Hz, IH), 7.10 2H), 2.77 – 2.65 (m,2H), 2.08 – 2.06 (m, 3H). LCMS M/Z (M+H) 341.

According to the analysis of related databases, 341988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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 87 N’-(2-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Palladium hydroxide (one small spatula) was added to a solution of the crystal (100 mg, 0.29 mmol) of the compound prepared in Example 86 (mixed with 4-aminophthalimide) in DMF, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60min. After the completion of the reaction, the reaction solution was filtered through Celite, and washing with ethyl acetate was carried out. Water was then added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure. Methanol was added to the residue, followed by filtration to give the title compound as a crystal (27 mg, 29.7%). MS m/z: 310 1H-NMR delta: 4.19 (2H, d, J = 5.37 Hz), 5.09 (2H, s), 6.52 (1H, t, J = 7.32 Hz), 6.63 (1H, d, J = 7.32 Hz), 6.72 (1H, t, J = 5.73 Hz), 6.97 (1H, dt, J = 1.46, 7.56 Hz), 7.04 (1H, d, J = 7.56 Hz), 7.59 (1H, dd, J = 1.95, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 8.01 (1H, d, J = 1.95 Hz), 9.28 (1H, s), 11.08 (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 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methoxyindoline (202 mg, 1.35 mmol) and N,N-diisopropylethylamine (0.34 mL, 2.0 mmol) in 4.0 mL of dry dichloromethane was added benzoyl chloride (0.23 mL, 2.0 mmol) at 0 C. After the reaction mixture was stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 70/30) to obtain 5-methoxy-1-benzoylindoline (224 mg, 65%).

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, 5-Methoxyindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY; US2011/294850; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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.

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, m.p. 196-198 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloroisatin, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4730004; (1988); 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. 1914-02-9, name is 3,3-Dimethylindoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H13N

Example 1 N-(3,3-Dimethylindolin-1-yl)-3-(4-imidazolyl)propionamide monohydrochloride (E1) A suspension of 3-(4-imidazolyl)propionic acid monohydrochloride (2.0g) (Chem. Ber. 66 , 156 [1933]) in thionyl chloride (10ml) and DMF (3 drops) was stirred at room temperature for 3h. The excess thionyl chloride was removed by rotary evaporation and the residue re-evaporated with 2 x 50ml of dry toluene. The residue was suspended in CH2Cl2 (100ml) and a solution of 3,3-dimethyl indoline (1.7g) and triethylamine (4ml) in CH2Cl2 (50ml) was added with stirring and cooling. The reaction mixture was stirred overnight, washed with saturated NaHCO3 and the lower organic layer dried (Na2SO4). Concentration of the organic extracts afforded the crude product which was purified by column chromatography on silica, eluding with CHCl3 containing increasing quantities of methanol.

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 1914-02-9.

Reference:
Patent; BEECHAM GROUP PLC; EP387431; (1990); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1074-82-4, 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 1074-82-4 as follows.

Synthesis of Compound 32.1 [0281] To a solution of potassium l,3-dioxoisoindolin-2-ide (18.5 g, 0.1 mol, 1.0 eq) in acetone (200 mL) was added 1,6-dibromohexane (43.5 g, 0.18 mol, 1.8 eq). The mixture was stirred at 65 C for 12 h. After cooling down, the mixture was filtered to remove the precipitated salt. The filtrate was concentrated and the residue purified by a short silica gel column (PE : EA = 10 : 1) to remove the excess 1,6-dibromohexane. 16.1 g of 32.1was obtained as a yellow oil (yield: 52%). 1H NMR (400MHz, DMSO- 6)D delta: 7.88-7.82 (m, 4H), 3.58-3.49 (m, 4H), 1.81-1.74 (m, 2H), 1.63-1.55 (m, 2H), 1.44-1.27 (m, 4H); ESI-MS (M+H) +: 312.1.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, 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 7147-90-2 as follows.

The intermediate compound 4 (0.0165 mol) was dissolved in 40 ml of methylene chloride, cooled to 0 C in an ice bath and triisopropylchlorosilane (0.1818 mol) was added under nitrogen, triethylamine (0.0182 mol) Heated at 40 C for 6 hours and cooled to room temperature. The filter cake was washed with dichloromethane. The filtrate was washed three times with 10% hydrochloric acid solution in 20 ml, and the mixture was washed three times with 20 ml of water. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was steamed to remove the solvent. The residue was washed with a small amount of methanol,Filtered to a yellow solid which was used directly in the next step without purification.

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Di-tert-butyl dicarbonate (54.6 g, 0.25 mol) and sodium hydrogen carbonate (75.6 g, 0.90 mol) were added to a solution of 5-nitroindolin-2-one (17.8 g, 0.10 mol) in 1500 mE THF at room temperature in a nitrogen atmosphere and were stirred for 67 h. The mixture was then stirred for a further 50 h at 50 C., and the reaction solution was then filtered. The filtrate was evaporated until dry, and water was rubbed into the residue, which was then sucked away again and rinsed again with watet Afier the drying in a vacuum, tert-butyl 5-nitro-2-oxo-indolin-1 -carboxylate in the form of a light-brown powder was obtained (20.8 g, 75%). ?RNMR (300 MHz, d6-DMSO): oe=1.61 (s, 9R,tHu), 3.87 (s, 2R, H2), 7.89 (d, 1R, H7), 8.20 (s, 1R, H4),8.25 (d, 1R, H6). ?3C NMR (100 MHz, DMSO): 28.0 (CR3), 36.3(C2), 84.8 (C(CH3)), 114.9 (C7), 120.1 (C4), 124.4 (C6),126.5 (C9), 143.8 (C5), 146.6 (C8), 148.8 (C=O), 177.0(C2).

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Schoenebeck, Jan-Michael; (23 pag.)US2017/165166; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem