Tag: M.W=100-200

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. 71294-03-6, name is 7-Fluoroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 7-Fluoroindolin-2-one

a) 7-Fluoro- 1 ,3,3-trimethylindolin-2-one To a suspension of NaH (8.79 g, 220 mmol) in tetrahydrofuran (100 ml) was added 7- fluoroindolin-2-one (8.30 g, 54.9 mmol) in portion within 20 minutes. The reaction mixture was stirred for 30 minutes. Mel (31.2 g, 13.7 ml, 220 mmol) was added dropwise at 24-27C within 1.5 hours. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was very carefully quenched with 20 ml saturated aqueous ammonium chloride solution at 10-15C, then diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as orange crystals (9.91 g). MS ESI (m/z): 194.3 [(M+H)+]. 1H NMR (CDC13, 400 MHz): (ppm) = 6.99-6.97 (m, 3H), 3.43 (d, J = 2.62 Hz, 3H), 1.37 (s, 6H).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

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;,
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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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Chloroisatin

General procedure: To a well-stirred solution of aldehyde 1 or isatin 4 (2 mmol) and tetronic acid 2(4 mmol) in ethanol (5 mL) was added sulfamic acid (20 mol percent) with continuous stirring. With the progress of the reaction, a yellowish solid separated out. Upon completion of the reaction (TLC), the resultant solid was filtered, washed with ethanol and dried. The resultant bis-tetronic acid 3/5 was found to be pure and did not require any further purification.

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:
Article; Pandit, Kapil S.; Desai, Uday V.; Wadgaonkar, Prakash P.; Kodam, Kisan M.; Research on Chemical Intermediates; vol. 43; 1; (2017); p. 141 – 152;,
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Application of 56341-39-0, 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. 56341-39-0 name is 6-Fluoroindolin-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.

At 130 C., 82.5 g of 6-fluoro-2-indolinone (starting material IV) are stirred in 180 ml acetic anhydride for 3 hours. After cooling to room temperature, the precipitate is filtered off with suction, washed with 100 ml of petroleum ether and dried. [0256] Yield: 64.8 g (61% of theory) [0257] Rf value: 0.75 (silica gel, petroleum ether/ethyl acetate=1:1) [0258] C10H8FNO2 [0259] Mass spectrum: m/z=192 [M-H]-

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

Reference:
Patent; Boehringer Ingelheim Pharma GmbH & Co. KG; US2005/43389; (2005); 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. 25369-33-9, name is 7-Chloroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 25369-33-9

To a cooled (0 C.) solution of 7-chloroindolin-2-one (1.0 g, 6.0 mmol) in TFA (11 mL) was added N-bromosuccinimide (1.0 g, 6.0 mmol) portion wise, and the resulting mixture was stirred at 0 C. for 6 h. The solvent was removed in vacuo and the residue was diluted and evaporated successively with DCM (25 mL) and EtOAc (25 mL). The crude product was triturated with EtOH to provide the title compound as a white solid (861 mg, 58% yield). MS (ESI): mass calcd. for C8H5BrClNO, 244.9; m/z found, 246.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 10.92 (s, 1H), 7.52-7.48 (m, 1H), 7.38 (d, J=1.2 Hz, 1H), 3.62 (s, 2H).

According to the analysis of related databases, 25369-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Laforteza, Brian Ngo; Lebold, Terry Patrick; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; (70 pag.)US2018/111942; (2018); A1;,
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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 366453-22-7 as follows. Recommanded Product: 4-Methoxyisoindolin-1-one

To an ice-cold solution of 2c (291 mg, 1.78 mmol) in CH2Cl2 (20 mL) was added a 1.0 M BBr3 solution in CH2Cl2 (3.6 mL, 3.6 mmol). The cold bath was then removed and the resulting solution was stirred for 16 h at ambient temperature. The reaction was carefully quenched by addition of water and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), filtered and evaporated to dryness to give 2d (232 mg, 87% yield) as beige solid.

According to the analysis of related databases, 366453-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim (Canada) Ltd.; US2004/106791; (2004); A1;,
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Application of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.57 2-((2-(2-(Hex-5-en-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (5C) White powder, mp 133-135 C, 80% yield; 1H NMR (400 MHz, CDCl3): delta 1.94 (s, 3H, CH3), 2.33-2.39 (m, 4H, 2 * CH2), 3.83 (s, 2H, CH2, thiazolidinone), 4.96-4.98 (m, 1H, =CH2), 5.02-5.07 (m, 1H, =CH2), 5.73 (s, 2H, ArCH2), 5.81-5.87 (m, 1H, CH=), 7.74-7.76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 59-48-3

To the solution of 28a (500mg, 3.76mmol) in acetonitrile (8mL) cooled to – 100C, was slowly added N-bromosuccinimide (770mg, 4.33mmol) with stirring. After the addition was complete, the mixture was stirred for Ih at -1O0C, then warmed to O0C for 2h. The resulting precipitate was collected by filtration, washed with water and dried under vacuo to give 28b (513mg, 64.4%).

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
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Electric Literature of 15861-23-1, 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 15861-23-1 as follows.

Intermediate 10tert-butyl 3-(5-cyanoindolin-l-yl)pyrrolidine-l-carboxylate[0109] To a solution of indoline-5-carbonitrile (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaC BH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; LI, Jinshui; JI, Jianguo; WO2012/22045; (2012); A1;,
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Related Products of 100510-65-4,Some common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

Step B: 6-(4-(2,2-Difluoroethylamino)furo[3,2-i/|pyrimidin-2-ylamino)-3,3-dimethylindolin- -oneTo a vial was added Pd2dba3 (0.235 g, 0.257 mmol), Cs2C03 (2.37 g, 7.28 mmol) and Ru-Phos (0.240 g, 0.514 mmol) in i-AmOH (8.00 mL). The mixture was evacuated and purged with N2. The mixture was stirred at about 65 C for about 20 min. 2-Chloro-A^-(2,2-difluoroethyl)furo[3,2- i/]pyrimidin-4-amine (1.00 g, 4.28 mmol) and 6-amino-3,3-dimethylindolin-2-one (0.754 g, 4.28 mmol, Astatech) were added in one portion. Additional i-AmOH (12.00 mL) was added. The mixture was evacauted and purged with N2. The mixture was stirred at about 70 C for about 5 h, stirred at about 60 C for about 15 h and then stirred at about 75 C for about 2 h. The mixture was cooled to rt and filtered. The precipitate was washed with DCM (20 mL) and MeOH (20 mL). The combined filtrate was concentrated and purified by column chromatography eluting with 25-65% EtOAc/heptane (40 g silica gel) to give a crude material. The material was suspended in Et20 (about 15 mL) and sonicated. The suspension was filtered and washed with Et20 (50 mL), then with DCM (about 30 mL). The precipitate was dissolved in DCM (50 mL), combined with filtrate, concentrated under reduced pressure, dissolved in MeOH (40 mL), and adsorbed onto silica gel (MeshNo. 200-400, 60A; 3 g). The material was purified by column chromatography eluting with 0 to 28% of 10% MeOH/DCM and DCM (40 g silica gel) to give a solid. The solid was purified by mass-triggered HPLC (Table 2, Method x) purification to give 6- (4-(2,2-difluoroethylamino)furo[3,2-i/]pyrimidin-2-ylamino)-3,3-dimethylindolin-2-one(0.397 g, 25%): LC/MS (Table 2, Method c) R, = 1.75 min.; MS m/z: 374 (M+H)+. Syk IC

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
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Electric Literature of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The chemical industry reduces the impact on the environment during synthesis 7-Fluoroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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