Category: 141452-01-9

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., Formula: C10H11NO2

To a solution of methyl indoline-5-carboxylate (200 mg, 1.13 mmol) and acetone (0.17 mL, 2.2 6mmol) in dichloromethane (10 mL) was added acetic acid (0.39 mL, 6.77 mmol). The reaction mixture was stirred at room temperature for 30 minutes before cooling to 0 C in an ice-water bath. Sodium cyanoborohydride (213 mg, 3.39 mmol) was added in 3 portions. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (30 mL), washed with saturated solution of NaHCCh (3 x 30 mL) followed by brine (30 mL) and then dried over anhydrous MgS04. Purification by column chromatography (0-70% ethyl acetate in cyclohexane) gave methyl 1 -isopropylindoline-5-carboxylate (45 mg, 0.21 mmol, 18% yield) as a colourless oil. LCMS: MS m/z 220.1 [M+H]+; 1H NMR (400 MHz, DMSO) d 7.64 (dd, J = 8.4, 1.8 Hz, 1H), 7.52 (d, J = 1.5 Hz, 1H), 6.44 (d, J = 8.4 Hz, 1H), 3.96-3.84 (m, 1H), 3.45 (t, J = 8.7 Hz, 2H), 2.93 (t, J = 8.6 Hz, 2H), 1.1 1 (d, J = 6.6 Hz, 6H).

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.

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. 141452-01-9, name is Methyl indoline-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H11NO2

Under the protection of argon, dissolve bis (trichloromethyl) carbonate (296mg, 1mmol) in 5mL of tetrahydrofuran, cool to 0 C, add triethylamine (202mg, 2mmol), stir for 5 minutes, and add indoline- Methyl 5-carboxylate 3a (177 mg, 1 mmol, prepared according to the published patent application “WO 2010149685”) was reacted at room temperature overnight. 20 mL of 2N dilute hydrochloric acid was added and extracted with dichloromethane (30 mL × 3). The organic phases were combined, washed with a saturated sodium bicarbonate solution (30 mL) and a saturated sodium chloride solution (30 mL), and the organic phase was dried over anhydrous sodium sulfate. , Filtered, and concentrated under reduced pressure to give 1- (chlorocarbonyl) indololine-5-carboxylic acid methyl ester 3b (239 mg, white solid), yield: 100%.

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.

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., HPLC of Formula: C10H11NO2

The indoline-5-carboxylate (177mg, 1.0mmol) was dissolved in pyridine (4mL), and4- (4- (2- (3- (chlorosulfonyl) benzamido) -4,5,6,7-tetrahydro-benzo [b] thiophen-3-carboxamido) phenethyl) benzoate (800mg, 1.26mmol),The reaction was heated to reflux for 18 hours.The reaction solution was diluted with ethyl acetate (80mL),0.1mol / L hydrochloric acid and washed (10mL ¡Á 3).The organic phase was dried over anhydrous sodium sulfate,concentrate.The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane (v / v) = 1/1) to give a yellow solid 491mg,Yield: 63.2%.

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; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Wang, Xiaojun; Yang, Xinye; Zhou, Pingjian; Yang, Chuanwen; Lin, Jihua; Xiong, Shaohui; Zhang, Yingjun; Xiao, Ying; Wang, Hui; Cao, Shengtian; Wu, Fangyuan; Ouyang, Luo; (74 pag.)CN105524053; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 141452-01-9, 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. 141452-01-9, name is Methyl indoline-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of Compound 113, 6-(pyridin-2-ylmethoxy)nicotinic acid[00135] LiOH (1 .345 M, 0.615 mL, 0.827 mmol) was added to a solution ofCompound 1 12 (0.101 g, 0.414 mmol) in THF (2 mL), followed by MeOH (0.6 mL) and the reaction mixture was stirred at rt for 26 h, concentrated to remove organic solvents, diluted with water, and washed with EtOAc (1 x). The aqueous phase was acidified to pH 2-3 with 2 M HCI, and the resulting precipitate was isolated by filtration, washed with water and dried to afford the title compound (79 mg, 83%) as a white solid.1H NMR (500 MHz, DMSO) 5 13.07 (s, 1 H), 8.71 (dd, J = 2.5, 0.8 Hz, 1 H), 8.56 (ddd, J = 5.0, 1 .8, 1 .1 Hz, 1 H), 8.19 (dd, J = 8.6, 2.4 Hz, 1 H), 7.81 (td, J = 7.7, 1 .7 Hz, 1 H), 7.46 (br d, J = 7.8 Hz, 1 H), 7.34 (ddd, J = 7.6, 4.8, 1 .1 Hz, 1 H), 7.04 (dd, J = 8.6, 0.8 Hz, 1 H), 5.50 (s, 2H). HRMS (ESI+): calcd for C12H11N2O3 (M + H)+, 231 .0764; found 231 .0760.

The chemical industry reduces the impact on the environment during synthesis Methyl indoline-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (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., SDS of cas: 141452-01-9

To a stirred solution of 4,6-dichloro-5-methylpyrimidine (101 mg, 0.62 mmol) in n- propanol (2.0 ml.) was added 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester {Bioorg. Med. Chem. Lett. 2008, 18, 5684 – 8) (100 mg, 0.56 mmol). The resulting yellow solution was heated at reflux (100 degrees Celsius). After 4 hours at reflux the reaction mixture was cooled to room temperature and was concentrated in vacuo. The reside was purified by flash chromatography, eluting with a gradient mixture of 10-40% ethyl acetate to heptane to give methyl 1-(6-chloro-5-methylpyrimidin-4-yl)indoline-5- carboxylate as a white solid (60 mg).

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

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. HPLC of Formula: C10H11NO2

1.26 g (5.8 mmoles) of di-tert-butyldicarbonate and 0.80 ml (5.8 mmoles) of Et3N are added successively at 20 C. to a solution of 0.85 g (4.8 mmoles) of methyl 5-indolinecarboxylate (J Heterocycl Chem (1993) 30 (4), 1133-1136) in 15 ml of CH2Cl2. The reaction mixture is stirred for 20 hours and concentrated to dryness under vacuum. The residue is divided between 50 ml of AcOEt and 25 ml of water. After stirring and decanting, the organic phase is washed with 25 ml of salt water, dried over MgSO4, filtered and concentrated to dryness under vacuum. The powder obtained is suspended in heptane, stirred and filtered in order to produce a white solid with a yield of 73%. Melting point=107-107.5 C.

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.

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6747024; (2004); B1;,
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.

Preparation of Compound 29, 1-tert-butyl 5-methyl indoline-1,5-dicarboxylate[0044] Di-tert-butyl dicarbonate (0.489 g, 2.24 mmol), followed by triethylamine (0.315 mL, 2.24 mmol) was added to a solution of Compound 28 (0.328 g, 1 .85 mmol) in dry DCM (5.8 mL) and the reaction mixture was stirred at rt for 26 hrs, concentrated. The residue was dissolved in EtOAc and washed with water (1 x), brine (1 x), dried (MgS04), filtered and concentrated. The crude material was recrystallized from hot EtOH to afford the title compound (373 mg, 73%) as a white solid. 1H NMR (500 MHz, CDCI3) delta 7.88 (d, J = 7.6 Hz, 1 H), 7.82-7.79 (m, 1 H), 4.02 (t, J = 8.7 Hz, 2H), 3.88 (s, 3H), 3.14 – 3.09 (m, 2H), 1 .57 (br s, 9H). Note that there also appears to be 2 extremely broad and weak singlets centred at 7.85 and 7.50 ppm which may be the missing aromatic CH. LRMS (ESI+): 178.09 (loss of Boc) and very weak 278.15

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; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

141452-01-9, name is Methyl indoline-5-carboxylate, 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. COA of Formula: C10H11NO2

To NaH (0.15 g, 3.75 mmol, 60% dispersion) at 0 0C, was added 19a (0.3 g, 0.95 mmol) in 5 mL of DMF. The mixture was stirred at 80 0C for 16h. The mixture was poured into a separatory funnel and DCM (50 mL), brine (50 mL) and 0.19M HCl (20 mL) were added. The layers were separated and the aqueous layer was extracted with DCM (3 x 50 mL). The combined extracts were washed with brine (2 x 50 mL), dried, filtered and evaporated. The residue was purified by preparative HPLC to afford 65 mg (25%) of 19b.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; TRAN, Joe, A.; CHEN, Chen; WO2010/149685; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature 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.

General procedure: To a 100-mL, one-necked, round-bottomed flask,sequentially charged with compound A (2.25 mmol, 1 equiv.), CS2 (11.25 mmol, 5 equiv.), K3PO4 (2.25 mmol, 1 equiv.) and 30 mL ofacetone. The mixture was stirred for 0.5 h at r.t. and then 4-(bromomethyl)benzoic acid (2.25 mmol, 1 equiv.) was added. TLCanalysis was used to indicate the completed reaction. The reactionmixture was concentrated to provide crude compound B.

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

Reference:
Article; Xie, Rui; Li, Yan; Tang, Pingwah; Yuan, Qipeng; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 320 – 333;,
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. 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. COA of Formula: C10H11NO2

A mixture of compound 24a (500 mg, 2.82 mmol), 1-bromo-4-fluoro-benzene 24b (0.31 mL, 2.82 mmol), Pd2(dba)3 (129 mg, 0.14 mmol), BINAP (132 mg, 0.21 mmol), and sodium t-butoxide (325 mg, 3.39 mmol) in toluene (25 mL) was placed in a capped vial and heated at 80 C. overnight. The reaction mixture was then diluted with EtOAc and water, and the water layer was basified to pH8 with 1N aqueous NaOH. The organic layer was concentrated under reduced pressure and purified by flash column chromatography (silica gel, 5-30% EtOAc/heptane) to give a mixture of compound 24c (145 mg), MS m/z (M+H+) 272.1, and compound 24d (232 mg), MS m/z (M+H+) 258.0.

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

Reference:
Patent; Zhang, Yue-Mei; Connolly, Peter J.; Lin, Shu-Chen; MacIelag, Mark J.; US2012/101081; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem