Category: 141452-01-9

Related Products 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.

General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ci-Ping; Jiang, Guo-Fang; Tetrahedron Letters; vol. 58; 18; (2017); p. 1747 – 1750;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 141452-01-9, 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. 141452-01-9, name is Methyl indoline-5-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Methyl 1- (3, 4, 5-Trimethoxy-benzyl)-2, 3-DIHYDRO-LH-INDOLE-5-CARBOXYLATE (21); [0193] To a solution of 20 (300 mg, 1.69 MMOL), 3,4, 5-trimethoxybenzaldehyde (365 mg, 1.86 MMOL) and dibutyltin dichloride (51 mg, 0.17 MMOL) in THF (8 mL) was added phenylsilane (229 ss 1.86 MMOL). The mixture was stirred overnight at room temperature under nitrogen. Additional aldehyde and PHENYLSILANE were added and the stirring continued until starting material was consumed. THF was evaporated in vacuum and the residue was purified by flash chromatography (eluent 20% EtOAc in hexane). The compound was further purified by re-crystallization in a mixture EtOAc/hexane and finally by a second flash chromatography (eluent 20% EtOAc in hexane) to give the title compound 21 (428 mg, 71%) as a white SOLID. H-NMR (DMSO) 8 : 2.96 (t, J = 8.4 Hz, 2H); 3.45 (t, J = 8.7 Hz, 2H); 3.61 (s, 3H); 3.71 (s, 6H); 3.72 (s, 3H); 4.30 (s, 2H); 6.59 (s, 2H); 6.61 (d, J = 8.4 Hz, 1H), 7.54 (d, J = 1. 6 Hz, 1H); 7.63 (dd, J = 1.8, 8.4 Hz, 1H).

The synthetic route of Methyl indoline-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METHYLGENE, INC.; WO2005/30704; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature 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.

In a 100 mL single-mouth bottle, dihydroindole-5-carboxylic acid methyl ester (800 mg, 4.50 mmol) was added and methanol was added.(15 mL) was dissolved, followed by the addition of potassium hydroxide (760 mg, 13.5 mmol), and reacted at 45 C for 15 h. After the reaction was completed,Dilute with 100 mL of water, then adjust the pH to 2 with 2M diluted hydrochloric acid, and use dichloromethane (50 mL×3).Drying and spinning off the solvent gave the title compound.

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; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Ge Chongxun; Huang Yiqiang; Cao Chen; Li Qingqing; Hou Shaohua; (63 pag.)CN108276382; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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.

(R)- l-(4-cyclopentyl- 1 ,3-dimethyl-2-oxo- 1 ,2,3,4-tetrahydropyrido [2,3-6] pyrazin-6- yl)indoline-5-carboxylic acid (i?)-6-chloro-4-cyclopentyl-l ,3-dimethyl-3,4-dihydropyrido[2,3-]pyrazin-2(lH)- one (42.0 mg, 0.15 mmol, 1 eq), methyl indoline-5-carboxylate (31.9 mg, 0.180 mmol, 1.2 eq), Pd2dba3 (6.9 mg, 0.0075 mmol, 5 mol%), XPhos (10.7 mg, 0.0225 mmol, 15 mol%) and K2C03 (82.9 mg, 0.60 mmol, 4 eq) were dissolved in tBuOH (1.5 mL, 0.1 M) and heated to 100 C for 20 hours. The mixture was filtered through celite, washed with DCM/EtOAc/MeOH and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-10%MeOH/DCM, 15 minute gradient) gave a mixture of the desired methyl ester and the (inconsequential) ethyl ester, which was used without further purification (65.56 mg). LCMS 40.48 (M+H), 435.47 (ethyl ester M+H). The resulting material was dissolved in THF (0.78 mL) and water (0.39 mL). LiOH (5.6 mg) was added and the mixture was stirred at room temperature. Due to poor solubility and sluggish conversion, an additional 5.6 mg LiOH, 0.39 mL water and 0.39 mL MeOH were added. After 2 days, the mixture was diluted with MeOH and purified by preparative HPLC to give a dark brown oil (33.84 mg, 0.08325 mmol, 53% over 2 steps. 1H NMR (400 MHz, Methanol-^) delta 8.11 (d, J= 8.6 Hz, 1H), 7.82 (dd, J= 8.6, 1.7 Hz, 1H), 7.76 (s, 1H), 7.23 – 7.16 (m, 1H), 6.24 (d, J= 8.5 Hz, 1H), 4.61 – 4.52 (m, 1H), 4.28 (q, J = 6.8 Hz, 1H), 4.06 (t, J= 8.8 Hz, 2H), 3.31 (s, 3H), 3.19 (t, J= 8.7 Hz, 2H), 2.09 (ddd, J = 17.1, 12.9, 8.7 Hz, 2H), 1.86 – 1.61 (m, 6H), 1.18 (d, J= 6.8 Hz, 3H). 13C NMR (100 MHz, cd3od) delta 169.88, 168.00, 150.16, 146.41, 132.06, 131.00, 126.64, 123.78, 121.72, 117.96, 112.26, 98.72, 58.11, 54.52, 50.70, 30.98, 30.72, 29.27, 27.49, 24.04, 23.33, 17.03. LCMS 407.48 (M+H).

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; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H11NO2

To a solution of 4,6-dichloropyrimidine (815 mg, 4.60 mmol) in n-propanol (12.0 ml.) was added 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester (Bioorg. Med. Chem. Lett. 2008, 18, 5684 – 8) (754 mg, 5.06 mmol). The resulting yellow solution was heated to reflux for 2 hours. After allowing the reaction to cool to room temperature, the reaction mixture was diluted with methyl te/t-butyl ether and then filtered. The collected solids were partitioned between chloroform and saturated aqueous sodium bicarbonate solution. The separated organic phase was dried over magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to afford 1-(6-chloro-pyrimidin-4-yl)- 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester (929 mg, 69.7 %) as an off-white solid. 1H NMR (400 MHz, deuterochloroform) delta 3.32 (t, J=8.49 Hz, 2 H) 3.91 (s, 3 H) 4.08 (t, J=8.69 Hz, 2 H) 6.67 (s, 1 H) 7.90 (d, J=0.98 Hz, 1 H) 7.96 (dd, J=8.49, 1.46 Hz, 1 H) 8.46 (d, J=8.59 Hz, 1 H) 8.65 (s, 1 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; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
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

Electric Literature of 141452-01-9, 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. 141452-01-9 name is Methyl indoline-5-carboxylate, 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.

(R)-l-(4-cyclopentyl-3-ethyl-l-methyl-2-oxo-l,2,3,4-tetrahydropyrido[2,3-6]pyrazin-6- yl)indoline-5-carboxylic acid (i?)-6-chloro-4-cyclopentyl-3-ethyl-l-methyl-3,4-dihydropyrido[2,3-]pyrazin- 2(lH)-one (20.2 mg, 0.0688 mmol, 1 eq), methyl indoline-5-carboxylate (14.6 mg, 0.0825 mmol, 1.2 eq), Pd2dba3 (3.2 mg, 0.00344 mmol, 5 mol%), XPhos (4.9 mg, 0.0103 mmol, 15 mol%) and K2C03 (38 mg, 0.275 mmol, 4 eq) were dissolved in tBuOH (0.69 mL, 0.1 M) and heated to 100 C for 18 hours. The mixture was filtered through celite, washed with DCM/EtOAc/MeOH and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-10%MeOH/DCM, 15 minute gradient) gave a mixture of the desired methyl ester and the (inconsequential) ethyl ester, which was used without further purification (29.64 mg). LCMS 434.48 (M+H), 449.47 (ethyl ester M+H). The resulting material was dissolved in THF (0.34 mL) and water (0.17 mL). LiOH (2.4 mg) was added and the mixture was stirred at room temperature. Due to poor solubility and sluggish conversion, an additional 2.4 mg LiOH, 0.17 mL water and 0.17 mL MeOH were added. After 2 days, the mixture was diluted with MeOH and purified by preparative HPLC to give a dark brown oil (16.78 mg, 0.0399 mmol, 59% over 2 steps. 1H NMR (400 MHz, Chloroform-;/) delta 8.10 (d, J= 8.6 Hz, 1H), 7.83 (dd, J= 8.6, 1.7 Hz, 1H), 7.79 – 7.74 (m, 1H), 7.16 – 7.1 1 (m, 1H), 6.21 (d, J= 8.4 Hz, 1H), 4.62 – 4.54 (m, 1H), 4.13 – 4.00 (m, 3H), 3.31 – 3.30 (m, 3H), 3.20 (t, J = 8.7 Hz, 2H), 2.14 – 2.04 (m, 2H), 1.80 – 1.54 (m, 8H), 0.86 (td, J = 7.6, 2.8 Hz, 3H). LCMS 421.51 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl indoline-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 141452-01-9, A common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

Reference Example 15 methyl 1-(6-chloropyrimidin-4-yl)-2,3-dihydro-1H-indole-5-carboxylate; A mixture of methyl 2,3-dihydro-1H-indole-5-carboxylate (5.19 g), 4,6-dichloropyrimidine (4.37 g), and ethanol (50 mL) was stirred overnight with heating under reflux, and concentrated under reduced pressure. To the residue were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the mixture was stirred for 30 min. Insoluble materials were collected by filtration to give the title compound (5.87 g, 69%) as a white solid. 1H-NMR (300 MHz, CDCl3)delta:3.32 (t, J=8.7 Hz, 2 H), 3.91 (s, 3 H), 4.08 (t, J=8.7 Hz, 2 H), 6. 66 (s, 1 H), 7.90 (s, 1 H), 7.95 (d, J=8.5 Hz, 1 H), 8.46 (d, J=8.5 Hz, 1 H), 8.64 (s, 1 H).

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
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 141452-01-9 as follows. SDS of cas: 141452-01-9

Preparation of Intermediate 1-(4′-Trifluoromethyl-biphenyl-2-carbonyl)-2,3-dihydro-1H-indole-5-carboxylic acid methyl ester (I-5b) 4′-Trifluoromethyl-biphenyl-2-carboxylic acid (4.51 g, 16.9 mmol) and 2,3-dihydro-1H-indole-5-carboxylic acid methyl ester I-5a (3.0 g, 16.9 mmol) were dissolved in DCM (50 ml). PyBroP (8.4, 18 mmol) and hunig’s base (2.58 g, 20 mmol) were added to the above mixture the reaction mixture was stirred overnight. PyBroP (4 g) was added to the reaction mixture and the reaction mixture was stirred overnight.The reaction mixture was diluted with DCM (200 ML) and washed with a saturated solution of NaHCO3 (100 ml*3), HCl (1N, 150 ml*2).The organic layer was collected and dried (Na2SO4).The solvent was removed under reduced pressure and the residue was purified by flash chromatography to provide the desired product 3.5 g.

According to the analysis of related databases, 141452-01-9, the application of this compound in the production field has become more and more popular.

Application 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.

To a solution of 10 (0.28 g, 1.58 mmol) in pyridine (2 mL), benzenesulfonyl chloride (0.40 ml, 3.16 mmol) was added. The reaction mixture was refluxed overnight. The mixture was then purified by silica gel chromatography (EtOAc:n-hexane=1:3) to afford 11 (0.40 g). 1H NMR (500 MHz, CDCl3): delta 2.99 (t, J=8.6 Hz, 2H), 3.87 (s, 3H), 3.97 (t, J=8.6 Hz, 2H), 7.45-7.48 (m, 2H), 7.56-7.59 (m, 1H), 7.66 (d, J=8.5 Hz, 1H), 7.75 (s, 1H), 7.82 (d, J=7.7 Hz, 2H), 7.90 (d, J=7.9 Hz, 1H).

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.