Tag: M.W=200-300

The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life. 15362-40-0

Pyrrole-2-carboxaldehyde (1 mmol) and 4-chlorobenzyl chloride (1.5 mmol) were reacted in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 – 25 C for 30 min. The progress of the reaction was monitored with TLC. After the completion, reaction was quenched by adding water and worked up by extraction with ethyl acetate (2 x 50 ml). The organic layers were combined, dried over Na2SO4 and distilled in vacuum to give N-(4-chlorobenzyl)pyrrole-2-carboxaldehyde (A) which was further purified by column chromatography using ethyl acetate: hexane (1:50). A (1 mmol) was reacted with 1-(2,6-dichlorophenyl)-2-indolinone (1.2 mmol) in the presence of piperidine (0.2 mmol) in CHCl3/ DMF under microwave irradiations at 100 C for 1h. The progress of the reaction was monitored with TLC. After completion, the reaction was worked up by adding water and extraction with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to give crude product 3c which was purified by column chromatography using ethyl acetate: hexane (3:50) as eluent. Yellow Solid, yield 70 %, mp 122-124 C; IR (KBr): 3054, 2928, 1698, 1600, 1485, 1367; 1H NMR (500 MHz, CDCl3) delta: 1H NMR (500 MHz, CDCl3, 25 C, TMS ) delta: 5.29 (s, 2H, CH2), 6.44-6.46 (m, 2H, ArH), 6.97-6.98 (m, 1H, ArH), 7.08-7.10 (m, 3H, ArH), 7.21 (t, 1H, J = 6.74 Hz, ArH), 7.31 (d, 2H, J = 8.48 Hz, ArH), 7.37-7.41 (m, 2H, ArH), 7.53 (d, 2H, J = 8.52 Hz, ArH), 7.71 (s, 1H, =CH), 8.25 (d, 1H, J = 7.4 Hz, ArH), 8.23 (dd, 1H, J = 4.37 Hz, 1.29 Hz, ArH) ; 13C NMR (125 MHz, CDCl3, normal/DEPT-135) delta: 50.4 (-ve, CH2), 109.0 (+ve, CH), 110.5 (+ve, CH), 116.5 (+ve CH), 117.4 (ArC), 117.8 (+ve, CH), 121.9 (ArC), 122.0 (+ve, CH), 122.4 (+ve, CH), 122.5 (+ve, CH), 124.8 (+ve CH), 127.1 (+ve, CH), 127.5 (+ve, CH), 128.1 (+ve, CH), 128.9 (ArC), 129.1 (+ve, CH), 129.3 (+ve, CH), 130.5 (+ve, CH), 133.8 (ArC), 135.5 (ArC), 135.8 (ArC), 141.3 (ArC), 164.8 (CF), 167.8 (C=O); HRMS (ESI) m/z for C26H17Cl3N2O [M+H]+ calcd. 479.0479, found 479.0421.

The chemical industry reduces the impact on the environment during synthesis 15362-40-0. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
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99365-40-9, Adding some certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, 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 99365-40-9.

Potassium tert-butoxide (6.2 g) was suspended in tetrahydrofuran (55 mL), and a suspension of 6-bromo-1,3-dihydroindole-2-one (2.3 g) in tetrahydrofuran (39 mL) and copper (I) bromide dimethyl sulfide complex (252 mg) were added. To the reaction mixture, methyl iodide (1.9 mL) was added at 0C, and then the reaction mixture was stirred at 0C for 5 minutes, and subsequently stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous solution of ammonium chloride was added, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.4 g) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 7.65 (1H, brs), 7.18 (1H, dd, J = 7.8, 2.0 Hz), 7.06 (1H, d, J = 2.0 Hz), 7.05 (1H, d, J = 7.8 Hz), 1.38 (6H, s). ESI-MS found: 240 [M+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 99365-40-9.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); A1;,
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Patent; JEPPESEN, LONE; ANDERSEN, HENRIK SUNE; OLSEN, OLE HVILSTED; JUDGE, LUKE MILBURN; HOLSWORTH, DANIEL DALE; BAKIR, FARID; AXE, FRANK URBAN; GE, YU; US2002/2199; (2002); A1;,
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118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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118289-55-7, 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 118289-55-7 as follows.

Preparation of 5- [2-[4-(1, 2- benzisothiazol-3-yl) -1-piperazipyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one (Ziprasidone base) Example 2 was repeated with the exception that 1-butyl-3-methylimidazolium tetrafluoroborate was used instead of 1-ethyl-3-methylimidazolium methyl sulfate. After the completion of the reaction the presence of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one was confirmed by HPLC.

According to the analysis of related databases, 6-Chloro-5-(2-chloroethyl)indolin-2-one, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KRKA; EP1889844; (2008); A2;,
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Adding some certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-2-one, 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 20870-78-4. 20870-78-4

Description 3:(Z)-3-{(1H-Pyrrol-2-yl)methylene)-5-bromoindolin-2-oneIn a 35 ml microwave tube were placed 5-bromo-1,3-dihydro-2H-indol-2-one (1 mmol), pyrrole-2-carbaldehyde (1.2 mmol), piperidine (2 drops), ethanol (10 ml) and a magnetic stir bar. The vessel was sealed with a septum and placed in the microwave cavity. Initial microwave irradiation of 200 W was used, the temperature being ramped from RT to 150 C. Once 150 C was reached the reaction vessel was held at this temperature for 30 min by moderation of the initial microwave power. After cooling, solvent was removed in vacuo and ethyl acetate was added to the reaction mixture. The precipitate was collected by filtration and washed with ethyl acetate (2x 10 ml) to afford a yellow-brown solid. The results set out below identify the product as the title compound D3.

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 5-Bromoindolin-2-one.

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
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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. 104618-32-8 name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, 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. 104618-32-8

EXAMPLE 14 3-Amino-6-n-butyloxy-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (1.12 g) with 4-n-butyloxyphenyl hydrazine hydrochloride (1.00 g) and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.47 g), mp 227-229 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, 6326-79-0

To a solution of 6-bromoindoline-2,3-dione (0.504 g,2.23 mmol)in acetonitrile (11 mL)was added K2C03 (1.23 g,8.92 mmol)then iodomethane (0.278 mL,4.46 mmol). The reactionmixture was heated at 60 oc for 1.5 h. After cooling to room temperature,water (30 mL)wasadded and the mixture was extracted with DCM (30 mL x 3). The combined organic layers were washed with brine (30 mL),dried over anhydrous Na2S04 and then concentrated in underreduced pressure to give the title compound (0.506 g,95%)that required no further purification.1HNMR(400MHz,CDCl3)87.46(dd,J=7.9,l.OHz,1H),7.32-7.28(m,1H),7.08(d,J=1.5 Hz,1H),3.25 (d,J = 0.6 Hz,3H).

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, 6-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
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A common compound: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2436-29-5

Step 3. 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4- yI)methyl)(methyl)amino)propyl)isoindoline-l,3-dioneTo a stirred solution of 9-((3aR,4R,6R,6aR)-2,2-dimethyl-6- ((methylamino)methyl)tetrahydrofuro[3,4-d][ l ,3]dioxol-4-yl)-9H-purin-6-amine (1.6 g, 5.0 mmol) and 3-(l,3-dioxoisoindolin-2-yl)propanal (2.0 g, 9.8 mmol) in 50 mL DCE was added NaBH(OAc)3 (3.18 g, 15.0 mmol). Then the mixture was stirred at rt overnight. Saturated NaHC03 aqueous solution was added to quench the reaction and the mixture was extracted with DCM (20 mL x 4). The organic phase was concentrated and the residue was purified by SGC (CH3OH : DCM = 1 : 100) to afford the title compound (2.47 g, yield: 94%) as white solid. NMR (500 MHz, MeOD): delta 8.26 (s, 1H), 8.21 (s, 1H), 7.77-7.84 (m, 4H), 6.15 (d, J = 2.5 Hz, 1H), 5.45-5.47 (m, 1H), 5.01-5.03 (m, 1H), 4.34-4.35 (m, 2H), 363-3.69 (m, 2H), 2.70-2.72 (m, 2H), 2.46-2.50 (m, 2H), 2.27 (s, 3H), 1.74-1.78 (m, 2H), 1.37 (s, 3H), 1.24 (s, 3H) ppm. MS (ESI): m/z 508.7 [M+l]+.

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, 2436-29-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
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181140-34-1, A common compound: 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To DMF solution (20 ml) of N-(2(R), 3-epoxypropyl)phthalimide 2.51 g (12.4 mmol), sodium azide 1.61 g (24.7 mmol) and ammonium chloride 0.79 g (14.9 mmol) were added, and stirred at 80 C. for 3 hours. The reaction mixture was allowed to stand at room temperature overnight. Benzene (50 ml) and distilled water (50 ml) were poured into the reaction mixture and organic layer was washed with water, brine sequentially, dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and filtrate was evaporated in vacuo. Further purification by silica gel chromatography gave 1.96 g of desired product. The NMR, FAB-MS spectra were consistent with the desired title intermediate. 1H-NMR(270 MHz,CDCl3)delta: 3.03(1H,d), 3.36-3.49(2H,m,), 3.85(2H,d), 4.05-4.13(1H,m), 7.73-7.78(2H,m), 7.84-7.90(1H,m). FAB-MS: m/z 247(M+H)+

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, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; Molecular Research Institute; US2006/14701; (2006); A1;,
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