Category: 41910-64-9

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, name: 4-Chloroindoline

Example 28b Synthesis of 2-[2-(4-chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-methylmorpholin-4-yl)-3H-pyrimidin-4-one 0.975 g of the sodium salt of [4-(2-methylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 1b, step 2b), 0.534 g of 4-chloroindoline, 0.57 ml of pyridine and 15 ml of DMF are placed in a round-bottomed flask, and then 0.9 g of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride is added. The reaction mixture is stirred at ambient temperature for 72 hours. The reaction mixture is poured into 50 ml of water, with stirring, and then the solid formed is filtered off through sintered glass and washed 3 times with approximately 15 ml of water, washed with 10 ml of EtOAc and rinsed with twice approximately 5 ml of diisopropyl ether, and the resulting product is left to air-dry under a hood. 2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-methylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (0.98 g) and characterized in the form of an off-white solid (yield 71%).LCMS ES+DMSO Tr 1.15; MH+m/z=389Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.82; [M+H]+: m/z 389; [M-H]-: m/z 3871H NMR spectrum (400 MHz): 1.06 (d, J=6.4 Hz, 3H); 2.48 (partially masked m, 1H); 2.80 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.40 to 3.50 (m, 2H); 3.76 (s, 2H); 3.81 (dd, J=3.0 and 11.5 Hz, 1H); 3.93 (m, 1H); 4.03 (m, 1H); 4.20 (t, J=8.7 Hz, 2H); 5.22 (s, 1H); 7.09 (d, J=8.1 Hz, 1H); 7.22 (t, J=8.1 Hz, 1H); 7.97 (d, J=8.1 Hz, 1H); 11.61 (broad s, 1H)

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, 4-Chloroindoline, other downstream synthetic routes, hurry up and to see.

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

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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

General procedure: to a suspension of iv (1mmol) in acetonitrile (10ml) was added 5-fluoroindoline (1.2mmol). The reaction mixture was stirred at 40C for 16h and then evaporated to dryness under reduced pressure. Water (10mL) and diethylether (15mL) were added and the resulting mixture was stirred for 5min. The precipitate formed was filtered off and dried to give 7 (86%) as a white solid.

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Certal, Victor; Halley, Frank; Virone-Oddos, Angela; Filoche-Romme, Bruno; Carry, Jean-Christophe; Gruss-Leleu, Florence; Bertin, Luc; Guizani, Houlfa; Pilorge, Fabienne; Richepin, Patrick; Karlsson, Andreas; Charrier, Veronique; Abecassis, Pierre-Yves; Vincent, Loic; Nicolas, Jean-Paul; Lengauer, Christoph; Garcia-Echeverria, Carlos; Schio, Laurent; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1506 – 1510;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 41910-64-9 as follows. name: 4-Chloroindoline

To a mixture of 4-chloroindoline (3 g, 19.53 mmol) in H20 (3 mL) was added 2- hydroxyacetonitrile (1.988 mL, 20.51 mmol). The reaction was heated at 105 C for 15 h. The mixture was diluted with EtOAc. The organics were washed with H20, dried over Na2S04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (3.3 g). LCMS m/z = 192.8 [M+H]+; NMR (400 MHz, CD3OD) delta ppm 3.02 (t, J = 8.2 Hz, 2H), 3.46 (t, J = 8.2 Hz, 2H), 4.28 (s, 2H), 6.60 (d, J = 2.1 Hz, 1H), 6.76 (d, J = 8.0Hz, 1H), 7.09 (t, J = 8.0 Hz, 1H).

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 4-chloroindoline (3 g, 19.53 mmol) in H2O (3 mL) was added 2-hydroxyacetonitrile (1.988 mL, 20.51 mmol). The reaction was heated at 105 C for 15 h. The mixturewas diluted with EtOAc and the organic portion washed with H2O, dried over Na2SO4, filtered, andconcentrated. The residue was purified by silica gel column chromatography to give the title compound(3.3 g). LCMS m/z = 192.8 [M+H]+; 1H NMR (400 MHz, CD3OD) delta ppm 3.02 (t, 2H, J = 8.2 Hz), 3.46 (t, 2H, J= 8.2 Hz), 4.28 (s, 2H), 6.60 (d, 1H, J = 2.1 Hz), 6.76 (d, 1H, J = 8.0 Hz), 7.09 (t, 1H, J = 8.0 Hz).

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

Reference:
Article; Ren, Albert; Zhu, Xiuwen; Feichtinger, Konrad; Lehman, Juerg; Kasem, Michelle; Schrader, Thomas O.; Wong, Amy; Dang, Huong; Le, Minh; Frazer, John; Unett, David J.; Grottick, Andrew J.; Whelan, Kevin T.; Morgan, Michael E.; Sage, Carleton R.; Semple, Graeme; Bioorganic and Medicinal Chemistry Letters; vol. 30; 5; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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.

Step 11b, Example 26b: (+)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one In a 25 ml round-bottomed flask, 42 mg of the sodium salt of [4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 9b) and 22 mg of 4-chloro-2,3-dihydro-1H-indole are placed in 1 ml of dimethylformamide and 0.2 ml of pyridine, and then 33 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added. The reaction medium is stirred at ambient temperature for 20 h, then evaporated, water is added, and the resulting mixture is triturated. The solid formed is filtered off, and rinsed successively with water, then with diisopropyl ether, with methylene chloride and then with pentane. The resulting solid is dried under vacuum for 2 h. (+)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (18 mg) in the form of a pulverulent solid (yield=31%).Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.66; [M+H]+: m/z 405; [M-H]-: m/z 4031H NMR spectrum (400 MHz): 2.58 (partially masked m, 1H); 2.83 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.27 to 3.52 (partially masked m, 4H); 3.77 (s, 2H); 3.82 to 3.96 (m, 2H); 4.12 (m, 1H); 4.21 (t, J=8.7 Hz, 2H); 4.71 (t, J=6.1 Hz, 1H); 5.20 (s, 1H); 7.09 (d, J=7.9 Hz, 1H); 7.22 (t, J=7.9 Hz, 1H); 7.97 (d, J=7.9 Hz, 1H); 11.61 (broad s, 1H)Optical rotation: alphaD=+19 C.=0.950 mg/0.5 ml in DMSO

Statistics shows that 4-Chloroindoline is playing an increasingly important role. we look forward to future research findings about 41910-64-9.

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

Synthetic Route of 41910-64-9, 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 41910-64-9 as follows.

General procedure: 5.1.25. 7-Fluoro-5-(methylsulfanyl)-2,3-dihydro-1H-indole (16f) To a stirred solution of potassium thiocyanate (14.0 g, 145 mmol) in MeOH (150 mL) was added bromine (3.80 mL, 72.3 mmol) dropwise at 0 C under N2 atmosphere. After the mixture was stirred for 15 min, a solution of compound 15f (9.00 g, 65.7 mmol) in MeOH (100 mL) was added and the resulting mixture was stirred at room temperature for 3 h. A solution of potassium hydroxide (18.4 g, 329 mmol) in water (120 mL) was added slowly to the mixture followed by stirring at 43 C for further 30 min. The reaction mixture was cooled to 10 C, and then iodomethane (4.10 mL, 65.7 mmol) was added. The resulting mixture was stirred at room temperature for 30 min. After the mixture was concentrated under reduced pressure, the residue was partitioned between CH2Cl2 and water. The organic layer was separated, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/CH2Cl2 = 2/1 to 1/1) to give the title compound (2.80 g, 23%). 1H NMR (400 MHz, CDCl3) delta 2.42 (3H, s), 3.05 (2H, t, J = 8.4 Hz), 3.62 (2H, t, J = 8.4 Hz), 6.85 (1H, d, J = 10.8 Hz), 6.93 (1H, s).

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sato, Kenjiro; Sugimoto, Hiromichi; Rikimaru, Kentaro; Imoto, Hiroshi; Kamaura, Masahiro; Negoro, Nobuyuki; Tsujihata, Yoshiyuki; Miyashita, Hirohisa; Odani, Tomoyuki; Murata, Toshiki; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1649 – 1666;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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.

A solution of XlntOI and an oxetane aldehyde derivative Y in methanol was stirred for 3 hours at room temperature. Sodium cyano borohydride was added at 0C and the mixture was stirred for another 3 hours at room temperature. The solvent was removed and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with water, brine solution, dried over sodium sulfate andconcentrated under reduced pressure to give the crude compound.Purification by column chromatography with 3% ethyl acetate / hexane yielded XYInt02.Synthesised according to the procedure disclosed in Example 1 where X is 4- chloro indole, Y is 3-hydroxyoxetane-3-carbaldehyde, and Z is 2- cyclopentylacetic acid. Formula: C19H23CIN203; Molecular Weight: 362.85; Mass/charge ratio: 362.14 (100.0%), 364.14 (32.7%), 363.14 (21.4%), 365.14 (6.7%), 364.15 (2.1 %); Elemental analysis: C, 62.89; H, 6.39; CI, 9.77; N, 7.72; O, 13.23.

Statistics shows that 4-Chloroindoline is playing an increasingly important role. we look forward to future research findings about 41910-64-9.

Reference:
Patent; AFFECTIS PHARMACEUTICALS AG; BOES, Michael; WO2012/163456; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 41910-64-9, 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 41910-64-9 as follows.

(1) Penta-O-acetyl-5-thio-D-glucopyranose (1323 mg) was suspended in ethyl alcohol (30 ml), and thereto was added sodium methoxide (28% methanol solution, 2 drops). The mixture was stirred at room temperature for one hour under argon atmosphere to give a solution of 5-thio-D-glucopyranose. To the solution were added 4-chloroindoline (500 mg) and ammonium chloride (174 mg), and the resultant mixture was refluxed for 22 hours. After being cooled to room temperature, the solvent was evaporated under reduced pressure to give crude 4-chloro-1-(5-thio-beta-D-glucopyranosyl)indoline, which was used in the subsequent step without further purification.

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tanabe Seiyaku Co., Ltd.; US2008/27014; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, category: indolines-derivatives

Step 10b, Example 25b: (-)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one In a 25 ml round-bottomed flask, 71 mg of the sodium salt of [4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 9b) and 38 mg of 4-chloro-2,3-dihydro-1H-indole are placed in 1 ml of dimethylformamide and 0.24 ml of pyridine, and then 57 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added. The reaction medium is stirred at ambient temperature for 20 h, then evaporated, water is added, and the resulting mixture is triturated. The solid formed is filtered off, and rinsed successively with water then with diisopropyl ether, with methylene chloride and then with pentane. The resulting solid is dried under vacuum for 2 h. (-)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one (62 mg) is isolated in the form of a pulverulent solid (yield=63%).Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.66; [M+H]+: m/z 405; [M-H]-: m/z 4031H NMR spectrum (400 MHz): 2.58 (partially masked m, 1H); 2.83 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.27 to 3.52 (partially masked m, 4H); 3.77 (s, 2H); 3.82 to 3.96 (m, 2H); 4.12 (m, 1H); 4.21 (t, J=8.7 Hz, 2H); 4.71 (t, J=6.1 Hz, 1H); 5.20 (s, 1H); 7.09 (d, J=7.9 Hz, 1H); 7.22 (t, J=7.9 Hz, 1H); 7.97 (d, J=7.9 Hz, 1H); 11.61 (broad s, 1H)Optical rotation: alphaD=-22 C.=0.351 mg/0.5 ml in DMSO

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroindoline, and friends who are interested can also refer to 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