Category: 22190-33-6

These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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. Synthetic Route of 22190-33-6

Step 2. fert-Butyl-5-bromoindoline-l-carboxylate (BI12): To a stirred solution of 5- bromo-indoline (3.0 g , 15mmol) in acetonitrile (100 ml), was added DMAP (0.185 g , 1.522 mmol) and di-ieri-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2X). The combined ether layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

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

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Career opportunities within science and technology are seeing unprecedented growth across the world, and those who study chemistry or another natural science at university now have increasingly better career prospects. Reference of 22190-33-6

A solution of the title A compound, 5-bromo-2, 3-DIHYDRO-1 H-INDOLE (15. 75 g, 79.54 mmol) in 200 mL acetonitrile and 200 mL dichloromethane is treated with DMAP (0.971 g, 7.95 mmol) and di-t-butyl dicarbonate (19.14 g, 87.49 MMOL). The solution is stirred at RT for 16 h. The mixture is diluted with 300 mL dichloromethane and washed twice with 1 N aqueous HCI and once with brine, dried over anhydrous MGS04, and concentrated to afford 5-bromo-2,3- dihydro-indole-1-carboxylic acid tert-butyl ester.

In the meantime we’ve collected together some recent articles in this area about 22190-33-6 to whet your appetite. Happy reading!

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65351; (2004); 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 22190-33-6 as follows. HPLC of Formula: C8H8BrN

REFERENCE EXAMPLE 8 1-boc-5-Bromoindoline 5-bromoindoline (10 g) was added in one portion to molten Boc-anhydride (11.6 g) at 30-40 C. Immediate effervescence was followed by the formation of a solid cake which was triturated with pentane to give the title compound (15 g) as a white powder.

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Reference:
Patent; Aventis Pharma Ltd.; Aventis Recherche Developpment; US6608084; (2003); B1;,
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 22190-33-6 as follows. Computed Properties of C8H8BrN

To a solution of 5-bromo-2,3-dihydro-1H-indole (2.11 g, 10.7 mmol) in 40 mL of THF was added Boc2O (2.56 g, 11.7 mmol). The reaction mixture was stirred at room temperature for 18 hours, and then concentrated under reduced pressure. Purification of the residue via flash chromatography (8% EtOAc in hexane) afforded 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.59 g, 95%) as a white solid; MS (M+H)=298.

According to the analysis of related databases, 22190-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Carter, David Scott; Schoenfeld, Ryan Craig; Weikert, Robert James; US2008/45543; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 22190-33-6, The chemical industry reduces the impact on the environment during synthesis 22190-33-6, name is 5-Bromoindoline, I believe this compound will play a more active role in future production and life.

5-Bromoindoline (3.96 g, 20 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.69 g, 22 mmol) and CH3CN (50 mL) were mixed and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (300 mL) and the organic solution was washed successively with water (50 mL), a 1 N HCl solution (50 mL), a saturated NaHCO3 solution (2×50 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. Trituration with hexane and drying in vacuo provided a white solid (2.26 g, 38% yield): 1H NMR (DMSO-d6, 300 MHz): 7.36 (s, 1H), 7.29 (d, 2H, J=7), 3.86 (t, 2H, J=7), 3.04 (t, 2H, J=7), 1.48 (s, 9H).

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

Reference:
Patent; Gilligan, Paul J.; US2006/63799; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 22190-33-6,Some common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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.

Procedure A: To a mixture of 5-bromoindoline (10.0 g, 50.8 mmol) in DCM (80 mL), was added a solution of di-tert-butyl dicarbonate (11.2 g, 51.3mmol) in DCM (20 mL). The reaction mixture was stirred at RT for 2 h and concentrated in vacuo to give tert-butyl 5- bromoindoline-1-carboxylate as a yellow oil (18.0 g, quantitative yield). LC-MS (ESI): m/z (M)+ = 297.12 / 299.33

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

Reference:
Patent; REMEDY PLAN, INC.; CRIMMINS, Gregory, Thomas; DE JESUS DIAZ, Dennise, Alexandra; BHURRUTH-ALCOR, Yushma; (483 pag.)WO2019/213570; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8BrN

A solution of 5-bromo-2,3-dihydro-1H-indole (4.97 g, 25.1 mmol), di-tert-butyl dicarbonate (6.0 g, 27.5 mmol) and 4-dimethylaminopyridine (catalytic) in dichloromethane (70 mL) was stirred at room temperature until the starting material was consumed. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel, eluted with ethyl acetate/hexane to give the product, 4.1 g (55%). 1H NMR (CDCI3) : delta 1.55 (s, 9 H), 3.06 (t, 2 H), 3.97 (t, 2 H), 7.23-7.27 (m, 2 H) and 7.72 (br m, 1 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 22190-33-6.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/69792; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6,Some common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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 stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2×). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22190-33-6, name is 5-Bromoindoline, 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 22190-33-6, Quality Control of 5-Bromoindoline

Step A: tert-Butyl 5-bromo-2,3-dihvdro-lH-indole-l-carboxylate To a stirred solution of 5-bromoindoline (320 mg, 1.62 mmol) in THF (8 mL) was added di-tert-butyl dicarbonate (529 mg, 2.42 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 90:10, to give the title compound.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; ZHAO, Lianyun; FRALEY, Mark; ZHU, Cheng; BIFTU, Tesfaye; BRNARDIC, Edward Joseph; WANG, Cheng; ZARTMAN, C. Blair; GALLICCHIO, Steven; NGUYEN, Diem; CROWLEY, Brendan; POTTEIGER, Craig; (257 pag.)WO2016/22644; (2016); 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 22190-33-6 as follows. Product Details of 22190-33-6

REFERENCE EXAMPLE 8 1-boc-5-Bromoindoline 5-bromoindoline (10 g) was added in one portion to molten Boc-anhydride (11.6 g) at 30-40 C. Immediate effervescence was followed by the formation of a solid cake which was triturated with pentane to give the title compound (15 g) as a white powder.

According to the analysis of related databases, 22190-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Ltd.; Aventis Recherche Developpment; US6608084; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem