Category: 22190-33-6

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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., name: 5-Bromoindoline

1,1-Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1-carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at room temperature. After 10 min, the mixture gradually became a suspension. After 3 hours, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and dried under house vacuum for 5 hours to give 1 ,1-Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1- carboxylate (ca. 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H),3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MEDINA, Jesus Raul; CHARNLEY, Adam Kenneth; ROMERIL, Stuart Paul; WO2015/56180; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6, 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. 22190-33-6 name is 5-Bromoindoline, 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.

1 , 1 -Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1 -carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at rt. After 10 min, the mixture gradually became a suspension. After 3 h, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and sucked under house vacuum for 5 h to give 1 , 1 -Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1 -carboxylate (ca 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) ppm 1 .50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H), 3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

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; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6, 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.

Step 1: Combine 5-bromoindoline (3.56 g, 18 mmol) and Et3N (1.92 g, 19 mmol) in CH2Cl2 (40 ml). Cool in an ice bath and add Boc2O (4.14 g, 19 mmol). Allow to warm, stir 2 h and add more Boc2O (0.50 g). Stir 2 h and wash with 1N HCl, then with 1N NaHCO3. Dry (MgSO4) and concentrate. Heat the solid with hexane, allow to cool, and filter to obtain the carbamate as off-white crystals, m.p. 124-6 C

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; Schering Corporation; US2004/220194; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 22190-33-6, 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.

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

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. Safety of 5-Bromoindoline

Part 1. To a solution of 5-bromoindoline (1.0 g, 5 mmol) in 10 ml of dioxane was added 5 mL of a 1N NaOH solution and 5 mL of water. This mixture was cooled with an ice bath, and di-tert-butyl dicarbonate (1.2 g, 5.5 mmol) was added in one portion. The reaction was allowed to warm to room temperature, stirred for 4 hours, and then concentrated. The residue was extracted with ethyl acetate (2*25 mL), and the combined organic phases were washed with water (2*25 mL), saturated aqueous NaCl (2*25 ml), then dried over MgSO4. Filtration and concentration in vacuo gave N-Boc-5-bromoindoline (1.33 g, 89%) as a light brown powder after drying. 1H NMR (CDCl3) delta: 1.541 (s, 9H); 3.03-3.08 (t, 2H); 3.92-3.96 (t, 2H); 7.23-7.27 (m, 3H).

The synthetic route of 5-Bromoindoline 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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromoindoline

Step 2. tert-Butyl-5-bromoindoline-1-carboxylate (BI12) To a stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in MeCN (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 Et2O 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 a off-white solid, which was used in the next step without further purification (3.0 g).

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.

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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., name: 5-Bromoindoline

Step 2. tert-Butyl-5-bromoindoline-1-carboxylate (BI12); 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 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 (2×). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as a off-white solid, which was used in the next step without further purification (3.0 g).

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, 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. Quality Control of 5-Bromoindoline

Combine 5-bromoindoline (3.56 g, 18 mmol) and Et3N (1.92 g, 19 mmol) in CH2Cl2 (40 ml). Cool in an ice bath and add Boc2O (4.14 g, 19 mmol). Allow to warm, stir 2 h and add more Boc2O (0.50 g). Stir 2 h and wash with 1N HCl, then with 1N NaHCO3. Dry (MgSO4) and concentrate. Heat the solid with hexane, allow to cool, and filter to obtain the carbamate as off-white crystals, m.p. 124-6 C.

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

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., category: indolines-derivatives

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).

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.

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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., category: indolines-derivatives

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 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 (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; US2014/171312; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem