Tag: M.W=300-400

Application of 105310-75-6, A common heterocyclic compound, 105310-75-6, name is cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide, molecular formula is C23H24N2O3, 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.

40% methyl amine solution (prepared by mixing methyl amine (210 g) with water (190 ml)) was added to (Z)-l -phenyl- l-diethylaminocarbonyl-2- phthalimidomethylcyclo propane compound of formula-6 (100 g) obtained from example-3 in toluene (450 ml) at 20-30C and stirred for 24 hours. After completion of the reaction both the organic and aqueous layers were separated; the aqueous layer was extracted with toluene. Both the organic layers were combined and washed with water. Carbon (8 g) was added to the organic layer, heated to 50-55C and stirred for 45 minutes. Filtered the reaction mixture and washed with toluene. Distilled off the solvent from filtrate under reduced pressure to get the title compound.Yield: 65 grams

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; MSN LABORATORIES LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; SATYANARAYANA, Revu; WO2012/46247; (2012); A2;,
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Adding a certain compound to certain chemical reactions, such as: 17826-05-0, name is 5,6-Dibromoindoline-2,3-dione, 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 17826-05-0, Formula: C8H3Br2NO2

To a solution of 1 (0.327) in THF (10 ml) a solution of 1 M BH3¡¤THF (2.5 equiv) was added dropwise at 0 C, then the mixture was stirred at rt for 3 h. After this time, the reaction was quenched by slowly adding 2 ml of demineralized water, then 2N HCl was added to pH 3. THF was removed under reduced pressure and the aqueous residue extracted with two portions of EtOAc. The organic layers were washed with two portions of brine, dried over Na2SO4 and evaporated under reduced pressure to give a yellow oil. The crude product was purified by silica gel chromatography (petroleum benzene/Et2O 9:1) to give the pure product 2 as a greyish crystalline solid, mp = 154-155 C, Rf = 0.2 (Et2O/petroleum ether 1:5), 68%. 1H NMR, 300 MHz, DMSO-d6 delta = 6.42 (1H, m, H3), 7.42 (1H, t, H2), 7.75 (1H, s, H7), 7.93 (1H, s, H4), 11.35 (1H, brs, NH). 13C NMR, 75 MHz, DMSO-d6 delta = 101.53, 113.62, 115.45, 116.71, 124.96, 128.76, 129.44, 136.35.

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, 5,6-Dibromoindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mollica, Adriano; Stefanucci, Azzurra; Feliciani, Federica; Lucente, Gino; Pinnen, Francesco; Tetrahedron Letters; vol. 52; 20; (2011); p. 2583 – 2585;,
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Electric Literature of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Using the same procedure, N-(8-bromooctyl)phthalimide was converted to 2-[8-(1H-imidazol-1-yl)octyl]-1H-isoindole-1,3(2H)-dione, mp 43¡ã-45¡ã C.

The chemical industry reduces the impact on the environment during synthesis 2-(8-Bromooctyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Cyanamid Company; US4610981; (1986); A;,
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Electric Literature of 1168150-46-6, A common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, molecular formula is C18H15NO4, 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.

N-methyl-2-(4-methylpiperazin-1-yl)-N-(5-amino-2-yl)acetamide (466m9,1.6mmo1) and (E) -3- (methyl group (phenyl) methylene) -2-oxo-indoline-6-carboxylate (500mg, 1.6mmol) placed in 15mL of methanol was heated to 70 C, 13h of holding, and then cooled to room temperature, washed with suction, the product of cold ethanol, and dried to give a bright yellow solid, methyl (Z)-3-((4-(N-cyclopropyl-2-(4-methylpiperazin-1-yl)acetylamino)anilino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (500mg, 80%).

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Hengli medical science and Technology Co Ltd; Luo, haoxian; Wang, aichen; (42 pag.)CN103848814; (2016); B;,
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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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(8-Bromooctyl)isoindoline-1,3-dione

A solution of an alkylbromide of general formula (VIII) (1 eq) in dry DMF (0.5 mL/mmol) was added to a flask suited for microwave heating. The amine (VII) (1 eq) was dissolved in DMF and added to the reaction flask and then K2CO3 (3 eq) was added. The reaction mixture was heated in a microwave oven at 7O0C for 3 h. The reaction was quenched with water, extracted with EtOAc and the organic phase concentrated to dryness, purified by chromatography using appropriate mixture of MeOH/CHCI3/NH3 to afford protected amines of general formula (IX).; Preparation 6: 2-(8-(cvclohexyl(3-morpholinopropyl)amino)octyl)isoindoline-l,3-dione (compound 6). General procedure 3. Starting materials: compounds 1 and 3. 1H-NMR (DMSOd6): delta 7.89-7.82 (m, 4H), 3.58-3.52 (m, 6H), 2.39-2.21 (m, HH), 1.71-1.08 (m, 24H).

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; Topotarget A/S; CHRISTENSEN, Mette Knak; BJOeRKLING, Fredrik; WO2010/142735; (2010); A1;,
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Related Products of 1337533-31-9, 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. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of terr-butyl 5-bromo-4-fluoroindoline-l-carboxylate (2.0 g, 6.33 mmol), 1- methyl-4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- IH-pyrazole (2.0 g, 9.49 mmol) and Na2CO3 (2.0g. 18.98 mmol) in dioxane / 1-120 (27 mL, 3: 1) was added [1,V-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (461 mg, 0.63 mmol). The mixture room temperature, the mixture was concentrated in vacuo. The crude residue was purified bysilica gel chromatography (petroleum ether EtOAc 1: 1) to give the title compound (1.5 g, 75%) as a brown solid.

The synthetic route of tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate has been constantly updated, and we look forward to future research findings.

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;,
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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. 153171-22-3, name is 2-(4-Bromobenzyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C15H10BrNO2

To a solution of 2-(4-bromo-benzyl)-isoindole-l ,3-dione (4.1 g, 13.1 mmol, 1.0 eq) in EtOH (50 mL) was added the Nu2 Eta42Omicron (3.3 g, 65.5 mmol, 5.0 eq). The reaction mixture was stirred for 1 h at rt The solvent was evaporated and water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2S04 and evaporated to give 4-bromo-benzylamine which was used without purified as a white solid (2.83 g, quant).

The synthetic route of 153171-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
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Related Products of 350797-56-7, 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. 350797-56-7, name is 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 360 mg of compound A was dissolved in 50 ml MeOH and was reduced using 10% Pd/C catalyst in a commercial H-Cube reactor. Solution was passed through catalyst cartridge at 40C at a rate of 1 ml/min. Pressure = 1 bar.Reaction was complete in 60 minutes. Solution was concentrated to give 37 mg (67% yield) of product. HNMR was satisfactory.

The synthetic route of 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RATIOPHARM GMBH; GIDWANI, Ramesh Matioram; KOLHATKAR, Mayur Vilas; WO2011/124704; (2011); A1;,
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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. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H15BrFNO2

1.1-dimethylethyl 4-fluoro-5-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)-2.3-dihydro-1H-indole-1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)*CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-dioxane (20 ml_) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 : 1 saturated aqueous NaCI: H20 (100 ml_) and ethyl acetate (100 ml_), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes, 40 g silica gel column) to afford 1 , 1- dimethylethyl 4-fluoro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H- indole- 1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1.51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 – 7.61 (m, 2 H).

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 1337533-31-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MEDINA, Jesus Raul; CHARNLEY, Adam Kenneth; ROMERIL, Stuart Paul; WO2015/56180; (2015); A1;,
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Electric Literature of 356068-93-4,Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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 9: Preparation of (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)- TV- (7-(hydroxyl-amino)-7-oxoheptyl)-2,4-dimethyl-lH-pyrrole- 3-carboxamide (Compound 15) Step 9a. (Z)-Methyl 7-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl- lH-pyrrole-3-carboxamido)heptanoate (Compound 110-15)To a stirred solution of compound 109 (220.0 mg, 0.73 mmol) in DMF (15 mL) at room temperature was added etaOBt (148.6 mg, 1.1 mmol), triethylamine(0.21 mL, 1.46 mmol), ECDI-etaC1 (210.2 mg, 1.1 mmol) and methyl 7- aminoheptanoate hydrochloride (157.1 mg, 0.8 mmol) successively. The mixture was stirred for 24 h at room temperature and was then diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL). The peta of the mixture was adjusted to 11-12 with 10 N NaOH. The mixture was filtered and the solid was washed with water, dried to obtain a crude product 110-15 as a yellow solid (0.3 g, 93.2%). LCMS: 442 [M+lf; 1H NMR(DMSO-^6): delta 1.31 (m, 4H), 1.50 (m, 4H), 2.31 (t, J= 7.35 Hz, 2H), 2.40 ( s, 3H), 2.42 (s,3H), 3.19 (m, 2H), 3.59 (s, 3H), 6.87 (m, 2H), 7.71 (m,3H), 10.91 (s, IH), 13.67 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
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