Tag: M.W=100-200

Electric Literature of 480-91-1, 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 480-91-1 as follows.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

According to the analysis of related databases, 480-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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Synthetic Route of 39603-24-2,Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,7-Dimethylindoline-2,3-dione, its application will become more common.

Reference:
Article; Dandia, Anshu; Khan, Shahnawaz; Soni, Pragya; Indora, Aayushi; Mahawar, Dinesh Kumar; Pandya, Prateek; Chauhan, Chetan Singh; Bioorganic and Medicinal Chemistry Letters; vol. 27; 13; (2017); p. 2873 – 2880;,
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Synthetic Route of 20870-79-5, 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. 20870-79-5 name is 5-Nitroindolin-2-one, 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.

To a mixture of 5-nitroindolin-2-one (Int 5a) (3.00 g, 16.8 mmol) in 1 ,2-dichloroethane (60 mL) was added phosphorus(V) oxybromide (4.59 g, 16.0 mmol). The mixture was heated to 90 C for 0.5 h. The mixture was cooled to just below reflux temperature. Imidazole (1.26 g, 18.5 mmol) was added and the mixture was heated to 90 C for 2 h. The mixture was cooled to rt and diluted with ice-water and sodium bicarbonate (solid). The mixture was extracted with DCM (4 x 100 ml_). The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by silica gel column chromatography (gradient PE to PE/EtOAc = 3:1 ) to afford the title compound as a yellow solid.

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

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; PINTO, Sheena; ANDERHUB, Simon; GEGE, Christian; DEUSCHLE, Ulrich; HOFFMANN, Thomas; (122 pag.)WO2020/21024; (2020); 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. 1914-02-9, name is 3,3-Dimethylindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 3,3-Dimethylindoline

To a vial containing 2-butyl-4-chloro-l-((5′-chloro-2′-cyano-[l, l’-biphenyl]-4- yl)methyl)- lH-imidazole-5-carboxylic acid (384b, 00 mg, 0.364 mmol) was added 2nd generation ruphos precatalyst (56.6 mg, 0.073 mmol) followed by sodium tert-butoxide (210 mg, 2.185 mmol). THF (3 mL) was added followed by 3,3-dimethylindoline (161 mg, 1.093 mmol). The reaction mixture was degassed with N2 and was then was sealed and heated at 65 C for 18 h. The reaction mixture was concentrated onto celite and purified by reverse phase ISCO (15 min gradient of 0- 100%B. A = H20/ACN/TFA 90: 10:0.1. B = ACN/H20/TFA 90: 10:0.1) to afford the title compound (405a, 70 mg, 0.107 mmol, 29.4 % yield) as an orange solid. LC-MS (Method A2): 1.07 min, [M + H]+=539.10.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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Reference of 39755-95-8, 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 39755-95-8 as follows.

Synthesis Example 90; ()-trans-6-Benzyl-3-hydroxy-2, 2-dimethyl-4-[(2-phenylethyl) amino] -2,3, 4,6-tetrahydro -pyrano [2, 3-findol-7-one ;N-Benzyl-5-methoxyisatin To a solution of 5-methoxyisatin (15.0 g, 84.7 mmol) in DMF (100 mL), sodium hydride (5.1 g, 127 mmol) and benzyl bromide (12.1 mL, 101.6 mmol) were added at 0C, and the resulting mixture was stirred for 1 hour. Water was added thereto, and the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with saturated aqueous ammonium chloride solution and then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to obtain the aimed product (yield : 96%). Brown solid 1 H-NMR (CDC13) 6 ; 3.77 (s, 3H), 4.91 (s, 2H), 6.67 (d, J= 8.5 Hz, 1H), 7.0-7. 1 (m, 1H), 7.15 (m, 1H), 7.25-7. 45 (m, 5H)

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; WO2005/90357; (2005); 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide, A new synthetic method of this compound is introduced below., Formula: C10H7NO3

To a solution of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetaldehyde (4.53 g) in EtOH (18 mL) was added a solution of 2-aminoethanthiol hydrochloride (2.9 g) in water (3.7 mL) followed by addition in one portion of potassium acetate (2.5 g). The reaction mixture was stirred at rt for 2 h and poured into a sat. NaHCO3 solution, the resulting precipitate was collected by filtration and washed with water and EtOH to yield the title compound as a white solid (4.92 g, 82percent).LC-MS: tR=0.57 min; [M+H]+=248.95

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aissaoui, Hamed; Boss, Christoph; Hazemann, Julien; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105491; (2011); A1;,
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Related Products of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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.

INTERMEDIATE 8 N-{3-[(4-Fluorophenyl)amino]pyridin-4-yl}-2-oxo-2,3-dihydro-1 H-indole-5- carboxamide2-Oxo-2, 3-dihydro-1 H-indole-5-carboxylic acid (200mg, 1.13mmol), Intermediate 5 (241 mg, 1.19mmol), HATU (644mg, 1.69mmol) and NEt^ (392uL, 2.82mmol) were dissolved in DMF (7.0ml_) and the reaction mixture heated at 60C for 2h. The reaction mixture was concentrated in vacuo, dissolved in EtOAc (50ml_), washed with water (40ml_). Brine (40ml_) was added to the organic phase and the biphasic mixture was filtered to give the title compound (409mg, 100%) as a brown solid. LCMS (ES+): 363.1 [MH]+. HPLC: Rt 4.23min, 79.8% purity.

Statistics shows that 2-Oxoindoline-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 102359-00-2.

Reference:
Patent; PROXIMAGEN LIMITED; PATIENT, Lee; SIMPSON, Iain; SAVORY, Edward; (51 pag.)WO2016/42332; (2016); A1;,
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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;,
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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;,
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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;,
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