Category: 15861-23-1

Reference of 15861-23-1,Some common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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 mixture of 4-(6-chloro-pyrimidin-4-yloxy)-piperidine-1 -carboxylic acid isopropyl ester (50.4 mg, 0.168 mmol) and 2,3-dihydro-1 H-indole-5-carbonitrile (22.0 mg, 0.15 mmol) in anhydrous 1 ,4-dioxane (2.0 ml.) was heated to 105 degrees Celsius. After stirring for 5 min, a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.184 ml_, 0.184 mmol) was added. After 30 minutes, the reaction mixture was quenched with saturated aqueous ammonium chloride and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous phase was extracted three times with dichloromethane, and the combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the crude residue was purified by column chromatography (20-60% ethyl acetate in heptane) to afford isopropyl 4-{[6-(5-cyano-2,3-dihydro-1 H-indol-1 -yl)pyrimidin-4-yl]oxy}piperidine-1 – carboxylate (38 mg, 61 %) as a white solid. 1H NMR (400 MHz, deuterochloroform) delta 1.25 (d, J=6.25 Hz, 6 H) 1.68 – 1.78 (m, 2 H) 1.96 – 2.04 (m, 2 H) 3.24 – 3.36 (m, 4 H) 3.78 – 3.87 (m, 2 H) 4.03 (t, J=8.79 Hz, 2 H) 4.89 – 4.97 (m, 1 H) 5.29 – 5.36 (m, 1 H) 5.96 (s, 1 H) 7.43 (s, 1 H) 7.51 (dd, J=8.79, 1.17 Hz, 1 H) 8.48 – 8.53 (m, 2 H). LCMS (ES+): 408.4 (M+1 ).

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

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

Electric Literature of 15861-23-1, 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 15861-23-1 as follows.

The compound of Part A (0.1 g, 0.694 mmol) was dissolved in 1,2-dichloroethane (DCE) (2.5 mL) and a solution of the compound of Part B (80 mg, 0.33 mmol) in DCE (1.5 mL) was added. This mixture was stirred for 10-15 min, then treated with sodium triacetoxyborohydride (0.1 g, 0.48 mmol) and stirred overnight at rt under N2. Reaction was quenched by addition of water and 1N NaOH, then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 4:1) provided the product (0.105 g, 86%). 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, 1H, J=7.5 Hz), 7.50-(t, 1H, J=7.5 Hz), 7.41 (t, 1H, J=7.5 Hz), 7.34-7.30 (m, 2H), 7.23-7.11 (m, 4H), 5.99 (d, 1H, J=8.4 Hz), 4.08 (dd, 2H, J=24.2, 15.8 Hz), 3.59 (s, 3H), 3.33 (m, 2H), 2.91 (t, 2H, J=8.4 Hz). LRMS m/z 369.0 (M+H)+ (API+). HRMS Calcd. for C24H21N2O2: 369.1603. Found: 369.1580.

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-23-1, A common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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 mixture of 5-cyanoindoline (70 mg, 0.487 mmol) and 2′-formylbiphenyl-2,4-dicarboxylic acid 4-ethyl ester 2-methyl ester (0.512 mmol) in 4 mL DCE was stirred for 10 min followed by addition of sodium triacetoxyborohydride (0.155 g, 1.5 eq.). Stirring was continued at rt overnight under N2. Reaction was quenched by addition of 1M NaOH then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over anh. Na2SO4, filtered and evaporated. Flash silica gel chromatography (hexane/ethyl acetate 85:15) provided the product (0.164 g, 76%) as a white, sticky foam. 1H NMR (CDCl3, 300 mHz) delta 8.58 (s, 1H), 8.14 (d, 1H, J=8.4 Hz), 7.36-7.30 (m, 4H), 7.18-7.13 (m, 4H), 6.00 (d, 1H, J=8.4 Hz), 4.44 (q, 2H, J=7.3 Hz), 4.07 (m, 2H), 3.64 (s, 3H), 3.29 (m, 2H), 2.90 (m, 2H), 1.44 (t, 3H, J=7.3 Hz). LRMS (API+) m/z 441.2 (M+H)+ [100].

The synthetic route of 15861-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 15861-23-1, 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 15861-23-1 as follows.

Intermediate 10tert-butyl 3-(5-cyanoindolin-l-yl)pyrrolidine-l-carboxylate[0109] To a solution of indoline-5-carbonitrile (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaC BH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; LI, Jinshui; JI, Jianguo; WO2012/22045; (2012); 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. 15861-23-1, name is Indoline-5-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H8N2

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 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.

These common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, 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. COA of Formula: C9H8N2

To a solution of indoline-5-carbonitrile (1 10 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.1 1 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

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

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. 15861-23-1, name is Indoline-5-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H8N2

To a solution of indoline-5-carbonitrile (0.6 g, 4.2 mmol) was added 50% aqueous hydroxylamine (0.275 g, 8.4 mmol). The reaction mixture was sealed and stirred overnight at 60 0C. After removal of the volatile solvent, the title compound was obtained (0.6 g) without further purification. LCMS m/z = 178.2 [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.

Synthetic Route of 15861-23-1, 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. 15861-23-1 name is Indoline-5-carbonitrile, 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.

The 5 – cyano – indoline (0.14 g, 1. 00 mmol) is added to dichloromethane (6 ml) in, adding pyridine (0.24 g, 3. 00 mmol) and intermediate 6 a (0.27 g, 1.000 mmol), Canada finishes after stirring at room temperature 1 hour. Concentrated under reduced pressure the crude intermediate 6 b directly used for the next step reaction.

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

Reference:
Patent; Chengdu Xiandao Pharmaceutical Development Co., Ltd.; Li Jin; Wang Wei; Chu Hongzhu; Lv Kaizhi; Liu Lichuan; Nong Yunhong; Chen Wei; (17 pag.)CN110256416; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-23-1, 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. 15861-23-1, name is Indoline-5-carbonitrile belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,3-dihydro-lH-indole-5-carbonitrile (8 g, 0.0556 mol; see step (iv) above) in DCM (50 mL) at 0C was added NN-dimethylaniline (13.5 g, 0.1112 mol) followed by 2-chloropropionyl chloride (8.46 g, 0.0667 mol). The reaction mixture was stirred for 3 h before being diluted with water and extracted with DCM. The organic layer was washed with water and brine, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography over silica gel to yield the sub-title compound as a pale yellow solid. Yield: 10.5 g.

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, Indoline-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/123748; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15861-23-1, name is Indoline-5-carbonitrile, 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 15861-23-1, name: Indoline-5-carbonitrile

A mixture of the compound of Part D (0.3 g, 0.72 mol) and 5-cyanoindoline (0.1 g, 0.694 mmol) in 2.5 mL 1,2-dichloroethane was stirred under N2 for 10 min, followed by the addition of sodium triacetoxyborohydride (0.22 g, 1.04 mmol, 1.5 eq.). The mixture was then stirred overnight at rt. The reaction was quenched by addition of water and 1M NaOH and extracted 3¡Á with CH2Cl2. Extracts were combined, washed with brine and dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 75:25) provided the desired alkylated product as a white foam (120 mg, 32%). 1HNMR (300 MHz, CDCl3) delta 8.27 (s, 1H); 7.93 (d, 1H); 7.30 (6H, m); 7.13-7.02 (6H, m); 6.18 (1H, bt), 5.88 (d, 1H, J=6 Hz); 5.03 (2H, dd, J=18, 10.8); 3.96, (s, 2H); 3.32 (t, 2H, J=6 Hz); 2.81 (t, 2H, J=6 Hz); 1.92 (m, 1H); 1.00 (6H, d, J=6.6 Hz). MS m/z 544.3 (M+H)+.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem