Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 825-70-7, name is 5-Fluoro-2-methylindoline, 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 825-70-7, Computed Properties of C9H10FN

Example 13c and Example 14c Synthesis of (+)-2-{2-[5-fluoro-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one and of (-)-2-{2-[5-fluoro-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one 430 mg of 5-fluoro-2-methyl-2,3-dihydro-1H-indole (reference example 4c, step 1c) and 872 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added to a solution of 743 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (obtained in step 2c of example 1c) in 25 ml of N,N-dimethylformamide and 25 ml of pyridine. The reaction mixture is stirred at ambient temperature for 48 hours and then 100 ml of water are added and the mixture is extracted with ethyl acetate. The organic phase is washed successively with a 0.1N hydrochloric acid solution, water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol (95/05: v/v), so as to give 580 mg of 2-{2-[5-fluoro-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one.The enantiomers are separated by chiral chromatography on a Whelk 01 SS, 10 mum column (10 mum, 80×350 mm), elution being carried out with a mixture of: heptane/dichloromethane/ethanol/methanol: 70/20/5/5; flow rate: 200 ml/min.252 mg of (+)-2-{2-[5-fluoro-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained, as first enantiomer, in the form of a white solid, the characteristics of which are the following:1H NMR spectrum (400 MHz): 1.26 (d, J=6.4 Hz, 3H); 2.70 (m, 1H); 3.34 to 3.48 (m, 5H); 3.60 (m, 4H); 3.71 (d, J=15.9 Hz, 1H); 3.91 (d, J=15.9 Hz, 1H); 4.73 (m, 1H); 5.20 (s, 1H); 7.00 (dt, J=3.0 and 9.1 Hz, 1H); 7.15 (dd, J=3.0 and 9.1 Hz, 1H); 7.95 (dd, J=5.0 and 9.1 Hz, 1H); 11.65 (broad m, 1H)Mass spectrometry: method ARetention time Tr (min)=0.72;[M+H]+: m/z 373; [M-H]-: m/z 371;Optical rotation: alphaD=+60.4 (c=1.939 mg/0.5 ml CH3OH)Then the second enantiomer, 246 mg of (-)-2-{2-[5-fluoro-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one, is obtained in the form of a white solid, the characteristics of which are the following:1H NMR spectrum (400 MHz): 1.26 (d, J=6.5 Hz, 3H); 2.69 (m, 1H); 3.35 to 3.47 (m, 5H); 3.60 (m, 4H); 3.71 (d, J=15.9 Hz, 1H); 3.91 (d, J=15.9 Hz, 1H); 4.72 (m, 1H); 5.20 (s, 1H); 7.00 (td, J=3.0 and 9.1 Hz, 1H); 7.15 (dd, J=3.0 and 9.1 Hz, 1H); 7.95 (dd, J=5.0 and 9.1 Hz, 1H); 11.66 (broad m, 1H)Mass spectrometry: method ARetention time Tr (min)=0.72;[M+H]+: m/z 373; [M-H]-: m/z 371;Optical rotation: alphaD=-57.9+/-1.1 (c=1.833 mg/0.5 ml CH3OH)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 603-62-3, 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. 603-62-3 name is 3-Nitrophthalimide, 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.

Step 1): An ice cooled solution of bromine (2.5 ml, 48.5 mmol) in 1N KOH aq.solution was added to the solution of 3-nitrophthalimide (9.66 g, 50 mmol) in 1N KOH aq.solution (150 ml) followed by 1N KOH at 0. The mixture was refluxed for 1.5 hours. After cooling, the mixture was neutralized with 2N HCl and stirred at 0 to precipitate 2-amino-6-nitrobenzoic acid, 6.23 g (68%): mp 190 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Nitrophthalimide, and friends who are interested can also refer to it.

Reference:
Patent; Grelan Pharmaceutical Co. Ltd.; Laboratoires Fournier S.C.A.; US5872115; (1999); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

To A NN-DIMETHYLFORMAMIDE/ACETONITRILE, (2 mL: 10 mL), mixture containing ethyldiisopropylamine (0.52 ML, 3 mmol) was added 2-oxoindoline-5-carboxylic acid (0.354 g, 2.0 mmol; described in: Sun L. et al. J. MED. Chem. 2000, 43 (14), 2655:), O- (BENZOTRIAZOL-1-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (0.77 g, 2.4 mmol) and 1-HYDROXYBENZOTRIAZOLE hydrate (0.324 g, 2.4 mmol) and stirred for 5 min at room temperature. Thereafter, 2- (AMINOMETHYL) pyridine (0.562 g, 5.2 mmol) was added and the resulting reaction mixture was stirred for 90 min followed by addition of a saturated aqueous NAHCO3 solution (10 ML). The solvents were removed in vacuo and 0.364 g (68% yield) of the title product was obtained as a white solid after purification on a silica gel column using chloroform/methanol, (9: 1), as the eluent : 1H NMR (DMSO-d6, 400 MHz) 8 10. 66 (s, 1 H), 8.96 (t, 7= 5. 6 HZ, 1 H), 8.55 (d, J = 4.4 Hz, 1 H), 7. 85 (d, J = 8. 0 HZ, I H), 7.83 (s, 1 H), 7. 78 (t, J = 7.6 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.29 (t, J= 6. 4 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 4.59 (d, J = 6.0 Hz, 2 H), 3. 58 (s, 2 H); MS (EI) MLZ 268 (M++1).

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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.

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 65 mg (42%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.30 (s, br, 1H, NH-1′), 12.05 (s, br, 1H, COOH), 10.67 (s, br, 1H, NH-1), 7.57 (s, 2H, H-vinyl, H-4), 7.12 (d, J=2.65 Hz, 1H, H-2′), 6.91 (d, J=7.82 Hz, 1H, H-6), 6.74 (d, J=7.82 Hz, 1H, H-7), 2.65 (t, J=6.94 Hz, 2H, CH2CH2COOH), 2.46 (t, J=6.94 Hz, 2H, CH2CH2COOH), 2.30 (s, 3H, CH3), 2.25 (s, 3H, CH3); MS m/z (relative intensity, %), 311 ([M+1]+, 100).

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 59-48-3, 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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1 H-NMR (360 MHz, DMSO-d6) delta 10.75 (s, br, NH), 7.83 (d, J=8Hz, 1H), 7.78 (s, 1H, H-4) 6.88 (d, J=8Hz, 1H),.3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

The synthetic route of Indolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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., Product Details of 7477-63-6

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

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; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

A solution of methyl indoline-5-carboxylate (200 mg, 1.13 mmol, 1.0 equiv.) in tetrahydrofuran (10 ml.) was cooled in an ice-water bath for 5 minutes. Sodium hydride (45 mg, 1.13 mmol, 1.0 equiv.) in tetrahydrofuran (2 mL) was added dropwise and the reaction was stirred for 20 minutes before the dropwise addition of iodomethane (0.07 mL, 1.13 mmol, 1.0 equiv.). The reaction mixture was stirred for 30 minutes before warming to 60 C for 24 hours. Additional sodium hydride (23 mg, 0.57 mmol, 0.5 equiv.) in tetrahydrofuran (1 mL) was added followed by iodomethane (0.04 mL, 0.57 mmol, 0.5 equiv.) in tetrahydrofuran (1 mL) and the reaction was stirred for a further 24 hours at 60 C. The reaction was cooled to room temperature and added dropwise to a saturated solution of NH4CI solution and extracted with ethyl acetate three times. The organics were combined, dried over anhydrous MgS04, filtered to remove the solids, and adsorbed onto silica. Purification by column chromatography (0-70% ethyl acetate in cyclohexane) gave methyl 1 -methylindoline-5-carboxylate (61 mg, 0.32 mmol, 28%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl indoline-5-carboxylate, its application will become more common.

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Product Details of 71294-03-6

Example 1 Preparation of 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one Variant A: 7-Fluoro-1,3-dihydro-2H-indol-2-one (100 g) is introduced as initial charge in 600 ml of N,N-dimethylacetamide and cooled to ca. 0 C. with ice/methanol cooling. A solution of potassium hydroxide (43.2 g) and potassium carbonate (143 g) in 600 ml of water is added and the mixture is briefly after-stirred. Then, 2-chloro-4,6-dimethoxy-1,3,5-triazine (140.8 g) is added and in each case 100 ml of water and N,N-dimethylacetamide are used for after-rinsing. The cooling bath is removed, the mixture heats up to ca. 30 C. It is stirred for 18 hours at room temperature. After adding 150 ml of toluene, dilute hydrochloric acid (ca. 700 ml) is used to adjust the pH to 3-4 and at the same time some antifoam (Fluowet PL 80) is added. The solid is filtered off with suction, washed three times with in each case 250 ml of water and twice with in each case 250 ml of heptane and dried in vacuo at 55 C. This gives the title compound as solid in a purity of 96.6% (187.5 g, 95% of theory). LC-MS: M+H=291 (100%). 1H NMR (400 MHz, DMSO-D6): delta (ppm)=11.37 (s, 1H), 7.64 (d, 1H), 6.97 (dt, 1H), 6.86 (dd, 1H), 4.05 (s, 6H).

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

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Karig, Gunter; Ford, Mark James; Siegel, Konrad; US2013/345422; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 39755-95-8,Some common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, molecular formula is C9H7NO3, 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.

One mmol of the compound of the structure represented by the formula (1-3)50% by weight aqueous solution of TBHP (in such an amount that the amount of TBHP is 0.8 mmol)And 1.5 mmol of K3PO4 were addedInto 5 mL of DMSO,At 20 , 500rpm stirring speed reaction 10h,Extraction with dichloromethane,Concentration and silica gel column chromatography (volume ratio of 3:2 dichloromethane / petroleum ether mixture as eluent) to isolate and purify,The compound of the structure shown by Formula (2-3) was obtained(0.39 mmol, 78% yield).

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

Reference:
Patent; Central China Normal University; Jia Fengcheng; Xu Cheng; Zhou Zhiwen; Wu Anxin; (9 pag.)CN107141292; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3891-07-4, A common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to about 7.26g 38mmol N- (2- hydroxyethyl) phthalimide of THF solution was dropwise added 40mL has dropped to -10 C, contains about 2.28g 57mmol NaH in 15mL THF was added dropwise. After completing -10 C under stirring for 30min. Then 4.2mL containing about 36.2 In THF 15mL mmol 4- chloro-acetoacetate was slowly dropwise added to the above system, a solution of After completion, the reaction system was naturally warmed to room temperature and stirred overnight. Under ice-cooling, ethanol was added 4mL quenched Off the reaction, the reaction solution was slowly poured into 100mL 1mol / L hydrochloric acid and ice, the aqueous phase was extracted with ethyl acetate, The combined organic phase was washed with saturated sodium bicarbonate solution, washed successively with water, dried over anhydrous sodium sulfate, filtered, The solvent was removed rotary evaporation, and the residue was purified by column chromatography to give compound S815.93g, yield 54%

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; JiangsuSimcere Pharmaceutical Company, Ltd; JiangsuSimcere Pharmaceutical Research Co. Ltd.; Chen, Rong; Liu, Fei; Cong, Xin; Feng, Lin; Li, Haidao; Dong, Qingli; (62 pag.)CN102464608; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem