Author: Jessica.F

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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., Computed Properties of C11H9NO3

Compound 359l-(3-((((2R^S,4R,5R)-5 6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyl)(isopropyl)amino)propyl)-3-(3-chlorophenyl)ureaStep 1. Preparation of 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)methyl)amino)propyl)isoindoline-l,3- dioneTo a solution of 2-(3-hydroxypropyl)isoindoline-l,3-dione (1.0 g, 4.88 mmol) in EA (50 mL) was added IBX (3.4 g, 12.19 mmol). The mixture was heated to reflux for 2h. After cooling, the mixture was filtered and the filtrate was concentrated to give 3-(l,3- dioxoisoindolin-2-yl)propanal crude (not weight), which was directly used for next step.To a solution of 9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)-9H-purin-6-amine (1.5 g, 4.90 mmol) and 3- (l ,3-dioxoisoindolin-2-yl)propanal (from last step) in DCE (50 mL) was added NaBH(OAc)3 (1.56 g, 7.30 mmol). The reaction mixture was stirred at rt overnight then saturated NaHC03 aqueous solution (50 mL) was added. The resulting mixture was extracted with DCM (50 mL x 2). The combined organic layers were dried over Na2S04 and concentrated. The residue was purified by SGC (DCM : MeOH = 100 : 1 to 10 : 1) to afford the title compound (1.38 g, yield: 57%) as a white solid. 1H NMR (500 MHz, MeOD): 58.30 (s, 1H), 8.23 (s, 1H), 7.85-7.79 (m, 4H), 6.17 (d, J = 2.5 Hz, 1H), 5.48 (dd, J = 2.5, 6.0 Hz, 1H), 5.03 (dd, J = 3.0, 6.5 Hz, 1H), 4.36 (t , J = 3.5 Hz, 1H), 3.67-3.65 (m, 2H), 2.94-2.89 (m, 2H), 2.62-2.60 (m, 2H), 1.82-1.79 (m, 2H), 1.60 (s, 9H), 1.39 (s, 3H) ppm; ESI-MS (m/z): 494.2 [M+l]+.

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; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
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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. 17630-75-0, name is 5-Chloro-2-oxindole, A new synthetic method of this compound is introduced below., COA of Formula: C8H6ClNO

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

The synthetic route of 17630-75-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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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. 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H11NO3

Compound 359l-(3-((((2R^S,4R,5R)-5 6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyl)(isopropyl)amino)propyl)-3-(3-chlorophenyl)ureaStep 1. Preparation of 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)methyl)amino)propyl)isoindoline-l,3- dioneTo a solution of 2-(3-hydroxypropyl)isoindoline-l,3-dione (1.0 g, 4.88 mmol) in EA (50 mL) was added IBX (3.4 g, 12.19 mmol). The mixture was heated to reflux for 2h. After cooling, the mixture was filtered and the filtrate was concentrated to give 3-(l,3- dioxoisoindolin-2-yl)propanal crude (not weight), which was directly used for next step.To a solution of 9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)-9H-purin-6-amine (1.5 g, 4.90 mmol) and 3- (l ,3-dioxoisoindolin-2-yl)propanal (from last step) in DCE (50 mL) was added NaBH(OAc)3 (1.56 g, 7.30 mmol). The reaction mixture was stirred at rt overnight then saturated NaHC03 aqueous solution (50 mL) was added. The resulting mixture was extracted with DCM (50 mL x 2). The combined organic layers were dried over Na2S04 and concentrated. The residue was purified by SGC (DCM : MeOH = 100 : 1 to 10 : 1) to afford the title compound (1.38 g, yield: 57%) as a white solid. 1H NMR (500 MHz, MeOD): 58.30 (s, 1H), 8.23 (s, 1H), 7.85-7.79 (m, 4H), 6.17 (d, J = 2.5 Hz, 1H), 5.48 (dd, J = 2.5, 6.0 Hz, 1H), 5.03 (dd, J = 3.0, 6.5 Hz, 1H), 4.36 (t , J = 3.5 Hz, 1H), 3.67-3.65 (m, 2H), 2.94-2.89 (m, 2H), 2.62-2.60 (m, 2H), 1.82-1.79 (m, 2H), 1.60 (s, 9H), 1.39 (s, 3H) ppm; ESI-MS (m/z): 494.2 [M+l]+.

The synthetic route of 883-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
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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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Safety of 2-Oxoindoline-5-carboxylic Acid

2-Oxo-3-(4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridin-1-ylmethylene)-2,3-dihydro-1H-indole-5-carboxylic acid A mixture of 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (44.5 mg, 0.25 mmol), 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde (41 mg, 0.25 mmol) and 0.1 mL of piperidine in ethanol (1 mL) was heated in a sealed tube at 80 C. for 6 hours. The precipitate was collected by vacuum filtration, washed with cold ethanol. The solid was then dissolved in methanol, the insoluble materials were removed and the filtrate was concentrated to give 20 mg (25%) of the title compound as a yellow solid. 1NMR (300 MHz, DMSO-d6) delta 13.59 (s, 1H, NH), 11.10 (br s, 1H, NH), 8.24 (s, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.65 (m, 2H), 7.37 (br s, 1H, NH), 6.78 (d, J=8.1 Hz, 1H), 3.38 (m, CH2), 3.0 (t, 2H, CH2). MS m/z 324 [M++1].

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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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19155-24-9, name is 3,3-Dimethylindolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 3,3-Dimethylindolin-2-one

Under an argon atmosphere, to a solution of 3,3-dimethylindolin-2-one (0.050 g, 0.31 mmol) in N,N-dimethylformamide (1.0 ml) was added sodium hydride (0.012 g, 60 wt percent oil dispersion) under ice-cooling. After stirring for 30 min, 2-(5-bromomethyl-2-chlorophenyl)-4-methoxy-6-phenyl-1,3,5-triazine (0.10 g, 0.26 mmol) obtained in the above-mentioned (1) was added, and the mixture was stirred at room temperature for 30 min. To the reaction mixture were added saturated aqueous ammonium chloride solution and ethyl acetate and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, washed with saturated brine, dried over sodium sulfate, filtered to remove sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=7/2) to give the title compound (0.11 g, yield 89percent). (0610) 1H-NMR (400 MHz, CDCl3) delta: 1.44 (6H, s), 4.18 (3H, s), 4.98 (2H, s), 6.72-6.76 (1H, m), 7.02-7.08 (1H, m), 7.13-7.19 (1H, m), 7.21-7.25 (1H, m), 7.31-7.36 (1H, m), 7.46-7.53 (3H, m), 7.55-7.61 (1H, m), 8.00 (1H, br s), 8.51-8.58 (2H, m).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; Nagamori, Hironobu; Mitani, Ikuo; Yamashita, Masaki; Hotta, Takahiro; Nakagawa, Yuichi; Ueda, Masatoshi; US2015/266834; (2015); 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. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Part A. To the product (1.0 g, 4.2 mmol) from Example 2, Part B, was added N,N-dimethylglycine (490 mg, 4.7 mmol), triethylamine (1.80 ml, 13 mmol), and DMF (30 mL). To this mixture was added benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate (2.2 g, 4.3 mmol). After 10 min, the clear yellow solution was poured into EtOAc (80 mL) and washed with H2O (2×50 mL). The organic layer was washed with brine, dried over Na2SO4, and filtered. The resulting residue was purified by radial chromatography (5% MeOH in CH2Cl2) to afford tert-butyl 5-[(N,N-dimethylglycyl) amino]-1-indolinecarboxylate (1.50 g, 110%) containing a small amount of DMF. LC/MS (ESI+): 320.1 (M+H)+.

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; Pinto, Donald J.P.; Han, Wei; Hu, Zilun; Qiao, Jennifer; US2003/232804; (2003); A1;,
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These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-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. Recommanded Product: 5,7-Dimethylindoline-2,3-dione

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
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Reference of 496-12-8, 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. 496-12-8, name is Isoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an oven-dried RB flask, 4-chloro-2-phenyl-1H-pyrrolo[3,2-c]pyridine 6b (250 mg, 1.09 mmol) and formaldehyde solution, 37 wt.% in H2O (0.2 mL, 2.73 mmol) were mixed in glacial acetic acid(5 mL). N-methyl piperazine (273.8 mg, 2.73 mmol, CAS 109-01-3)was added drop wise at 0C. The resulting mixture was stirred atroom temperature for 12 h. After completion of the reaction, the excess solvent was evaporated to dryness under reduced pressure.The residue was neutralized with 10% NaHCO3 solution, the solidf ormed was collected by filtration, washed with water and dried.The crude product was purified by silica gel column chromatographyto provide title compound as an off-white solid (326.3 mg,88%).

The synthetic route of Isoindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jose, Gilish; Suresha Kumara, Tholappanavara H.; Sowmya, Haliwana B.V.; Sriram, Dharmarajan; Guru Row, Tayur N.; Hosamani, Amar A.; More, Sunil S.; Janardhan, Bhavya; Harish; Telkar, Sandeep; Ravikumar, Yalegara Siddappa; European Journal of Medicinal Chemistry; vol. 131; (2017); p. 275 – 288;,
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Electric Literature of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (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. 84378-94-9, name is 4-Chloro-5-fluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C8H3ClFNO2

2-amino-5-fluoro-6-chlorobenzoic acid 0.01mol joined is provided with a reflux condenser, magneton, thermometer in three-necked bottle, adding toluene 15 ml, dry SOCl 2 3 ml, reflux 1h, stopping reaction, rotary evaporation under reduced pressure to remove the solvent and redundant SOCl 2. Then added to the flask 0.01moL of 5-fluoro-4-chloro Indoloquinone (5-fluoro-6-chloro Indoloquinone) and 15 ml of dichloromethane, to continue to reflux reaction 1h, cooling to room temperature, filtered, to obtain the yellow solid, washing with methanol, dichloromethane or toluene recrystallization

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; Northwest University; Huo, Baolong; Wang, Cuiling; (52 pag.)CN105330666; (2016); A;,
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