Category: 622392-04-5

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 622392-04-5 as follows. Safety of 2-Bromo-5-iodopyrazine

(1-((1-(trifluoromethyl)cyclobutyl)methyl)piperidin-4-yl)methanol (880 mg, 3.50 mmol) was dissolved in THF (30 mL). At 0 C., NaH (126 mg, 5.25 mmol) was added thereto, and stirred for 30 minutes. 2-bromo-5-iodopyrazine (1.09 g, 3.85 mmol) was added thereto, following with stirring at 55 C. for 10 hours. The reaction mixture was added with water, and extracted with EtOAc. The obtained organic layer was washed with saturated aqueous brine solution, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The obtained material was used without further purifying process

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; Lee, ChangSik; Jang, TaegSu; Choi, DaeKyu; Ko, MooSung; Kim, DoHoon; Kim, SoYoung; Min, JaeKi; Kim, WooSik; Lim, YoungTae; US2015/166480; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H2BrIN2

Description 66: 2-bromo-5-(trifluoromethyl)pyrazine (D66); Potassium fluoride (238 mg, 4.09 mmol) and copper(I) iodide (779 mg, 4.09 mmol) were mixed and heated under vacuum using heat gun (temperature 360 0C, on display of heating gun) for 20 minutes (until a greenish colour of the mixture appeared). After cooling at room temperature, DMF (4 ml) and NMP (4.00 ml) were added followed by (trifluoromethyl)trimethylsilane (0.603 ml, 3.77 mmol) and 2-bromo-5-iodopyrazine D65 (896 mg). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in 200 ml of 6N NH3 water solution and was extracted twice with Et2O(3 x 50 ml). Gathered Et2O layers were dried over Na2SO4.Diethyl ether was distilled by Claisen apparatus. It was recovered the title compound D66(586 mg).1H NMR (400 MHz, CHLOROFORM- d) delta ppm 8.73 – 8.81 (m, 1 H) 8.84 (s, 1 H)

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 622392-04-5,Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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.

(l-((l-(Trifluoromethyl)cyclobutyl)methyl)piperidin-4-yl)methanol (0.88 g, 3.50 mmol) was dissolved in THF (30 mL). At 0C, NaH (0.13 g, 5.25 mmol) was added thereto. The mixture was stirred for 30 minutes. 2-bromo-5-iodopyrazine (1.09 g, 3.85 mmol) was added thereto, followed by stirring at 55C for 10 h. To the reaction mixture, water was added, and the mixture was extracted with EtOAc. The organic layer was washed with saturated brine aqueous solution, dried with anhydrous MgS04, and then concentrated under reduced pressure. The obtained product was used without further purification. (1.40 g, 87%, colorless oil).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-iodopyrazine, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; KIM, Yuntae; LEE, ChangSik; CHOI, DaeKyu; KO, MooSung; HAN, Younghue; KIM, SoYoung; MIN, JaeKi; KIM, DoHoon; WO2015/80446; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 622392-04-5, name is 2-Bromo-5-iodopyrazine, belongs to pyrazines 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 622392-04-5, Recommanded Product: 2-Bromo-5-iodopyrazine

Preparation 62: Methyl {(2S)-1 -[(2S)-2-{4-[4-(5-bromopyrazin-2-yl)phenyl]-1 H-imidazol-2-yl}pyrrolidin- 1 -yl]-3-methyl-1 -oxobutan-2- l}carbamateMethod A:To a solution of methyl {(2S)-3-methyl-1-oxo-1-[(2S)-2-{4-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]-1 H-imidazol-2-yl}pyrrolidin-1-yl]butan-2-yl}carbamate obtained from Preparation 61 (33.00 g, 66.53 mmol) and 2-bromo-5-iodopyrazine obtained from Preparation 10 (24.70 g, 86.67 mmol) in 1 ,4- dioxane (600 mL) and water (150 mL), were added potassium phosphate (28.20 g, 133.01 mmol) and tetrakis(triphenylphosphine)palladium (0) (2.30 g, 1.99 mmol). The mixture was sparged with nitrogen for 10 minutes before heating to reflux for 16 hours. After this time, the reaction was allowed to cool to room temperature, the solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (250 mL) and water (250 mL). The layers were separated and the organic layer was washed with brine (500 mL), dried over magnesium sulphate. The solvent was removed under reduced pressure to give a black gum. The crude product was purified by flash chromatography (heptane : acetone, 20:80) to give the title compound as a foam ( 22.00 g).LCMS (run time = 25 minutes, System K) Rt= 13.19; m/z 527 and 529 [MH+]H NMR (400 MHz, CD3OD+drop of TFA) : delta= 8.99 (s, 1 H), 8.81 (s, 1 H), 8.25 (d, 2H), 7.94 (s, 1 H) 7.86 (d, 2H), 5.27-5.23 (m, 1 H), 4.24 (d, 1 H), 4.13-4.08 (m, 1 H), 3.88 (m, 1 H), 3.65 (s, 3H), 2.62-2.54 (m, 1 H), 2.31- 2.24 (m, 1 H), 2.20-2.14 (m, 2H), 2.09-2.00 (m, 1 H), 0.93 (d, 3H), 0.88 (d, 3H).

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, 2-Bromo-5-iodopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 622392-04-5, 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

In a 5 mL round bottomed flask were mixed: 1,1-dimethylethyl 1-piperazinecarboxylate (110 mg, 0.590 mmol, available from Fluke), 2-bromo-5-iodopyrazine (140 mg, 0.491 mmol, available from Apollo) and Dipea (0.112 mL, 0.639 mmol) in Tert-Butanol (2 mL). The reaction was stirred and heated under reflux at 100 C. for 40 hr. The reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL) and the organic layer washed with brine (20 mL) before being dried through an hydrophobic frit and concentrated. The samples were dissolved in 1:1 MeOH:DMSO 2×1 mL and purified by MDAP. The solvent was evaporated in vacuo to give the required product 1,1-dimethylethyl 4-(5-iodo-2-pyrazinyl)-1-piperazinecarboxylate (98.6 mg) LCMS (Method C): Rt=1.20, MH+=391

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-iodopyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

622392-04-5, name is 2-Bromo-5-iodopyrazine, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 2-Bromo-5-iodopyrazine

Preparation of compound 22a: 2-(2,2-difluoroethoxy)-5-iodopyrazineTo a solution of 2,2-difluoroethanol (0.74 g, 8.7 mmol) in THF (5OmL) at room temperature was added sodium butoxide (1.13 g, 11.4 mmol) and stirred for 15 min. The reaction mixture was cooled to 0 0C and a solution of 2-bromo-5-iodopyrazine (2.5 g, 8.7 mmol) in THF (50 ml_) was added slowly over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was diluted with ethyl acetate and washed with sat. NH4CI. The organic layer was dried over MgSO4, filtered and concentrated which gave the title compound 22a (2.3 g, 90%).

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 622392-04-5, A common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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.

EXAMPLE 25 Step 1. 2-iodo-5-methoxy-pyrazine. Sodium methoxide (25% wt. in MeOH,0.321 mL, 1.4 mmol) was combined with N-methyi pyrrolidine (NMP) (1.28 mL) and warmed to 60 C. 2-bromo-5-iodo-pyrazine (0.40 g, 1.4 mmol) was added. The suspension was stirred at 60 0C for 1 hour. Combined with an additional 100 mg previously run reaction prior to work-up. Reaction mixture was partitioned between H2O and ethyl acetate and the aqueous layer was extracted (3x) with ethyl acetate. The combined extracts were dried over MgSO4, filtered and concentrated to give a brown oil which solidified to obtain 406 mgs of crude material. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 3.90 (s, 3 H), 8.03 (d, J=1.4 Hz, 1 H), 8.29 (d, J=1.4 Hz, 1 H); MS (APCI+, m/z) 237.

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 PRODUCTS INC.; WO2007/72151; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-5-iodopyrazine

To a 250 ml_ flask were added 2-bromo-5-iodopyrazine (2.9 g, 10 mmol, 1 equiv.), di- te/f-butyl-9H-carbazole (3.0 g, 11 mmol, 1.1 equiv.), copper powder (640 mg, 10 mmol, 1 equiv.) and potassium carbonate (4.5 g, 30 mmol, 3 equiv.). The flask was degassed by three cycles of vacuum-nitrogen purging and 50 ml_ of chlorobenzene was injected. The mixture was stirred at 110 C for 10 h under a nitrogen atmosphere. After cooling, water was added to the reaction mixture followed by extraction with DCM (3 c 50 ml_). The combined organic layers were dried with anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography. DCM/Hexane=1/3 was used as eluent to afford Br-Pz-tCz as a faint yellow solid. Yield: 85%. Rf: 0.65 (33% DCM/Hexanes). Mp: 180-182 C. 1H NMR (400 MHz, CDCI3) d (ppm): 8.84 (d, J = 1.4 Hz, 1 H), 8.74 (d, J = 1.4 Hz, 1 H), 8.13 (dd, J = 2.0, 0.6 Hz, 2H), 7.84 (dd, J = 8.8, 0.7 Hz, 2H), 7.54 (dd, J = 8.7, 2.0 Hz, 2H), 1.49 (s, 18H). 13C NMR (101 MHz, CDCI3) d (ppm): 147.97, 145.94, 145.28, 139.30, 137.06, 134.57, 125.10, 124.37, 1 16.46, 1 10.73, 34.85, 31.87. HR-MS (LTQ Orbitrap XL) [M+H]+ Calculated: (Cz^z/NsBr) 436.1383, 438.1363; Found: 436.1380, 438.1359

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; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; ZYSMAN-COLMAN, Eli; CHEN, Dongyang; PACHAI GOUNDER, Rajamalli; (104 pag.)WO2019/202342; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – 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 622392-04-5 as follows. name: 2-Bromo-5-iodopyrazine

EXAMPLE 41C (endo)-3-(5-Iodo-pyrazin-2-yloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane Under N2, the mixture of (endo)-tropine (Aldrich, 1.54 g, 11 mmol) was treated with potassium t-butoxide (Aldrich, 0.96 g, 10 mmol) in THF (anhydrous, Aldrich, 50 mL) at ambient temperature for 1 h. The product of Example 41B (2.85 g, 10.0 mmol) and was added. The brown mixture was stirred at ambient temperature for 4 hours and quenched with water (5 mL). The mixture was concentrated and the residue was purified by chromatography (150 g SiO2, EtOAc:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) to give the title compound. 1H NMR (300 MHz, CD3OD) delta 2.16-2.60 (m, 8H), 2.84 (s, 3H), 3.78-4.05 (m, 2H), 5.17-5.40 (m, 1H), 8.14 (d, J=1.36 Hz, 1H), 8.42 (d, J=1.36 Hz, 1H) ppm; MS (DCI/NH3) m/z 346 (M+H)+.

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ji, Jianguo; Li, Tao; Lynch, Christopher L.; Gopalakrishnan, Murali; US2008/45539; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 622392-04-5, name is 2-Bromo-5-iodopyrazine, belongs to pyrazines 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 622392-04-5, SDS of cas: 622392-04-5

To a solution of 2-bromo-5-iodopyrazine (500 mg, 1.76 mmol), phenylacetylene (224 mg, 241 mu, 2.19 mmol, 1.25 equiv.), triethylamine (533 mg, 734 mu, 5.27 mmol, 3 equiv.),bis(triphenylphosphine)palladium (II) chloride (73.9 mg, 0.105 mmol, 0.06 equiv.) and triphenyl-phosphine (13.8 mg, 0.053 mmol, 0.03 equiv.) in 10 ml of THF was added under an Argon atmosphere copper (I) iodide (10.0 mg, 0.053 mmol, 0.03 equiv.). The suspension was warmed to 60C overnight, taken up in 5 ml of ethyl acetate and adsorbed on 4 g of silica.Purification by flash chromatography on silicagel using a 2: 1 ethyl acetate/heptane mixture yielded the title compound as a light brown solid (107 mg, 23% yield). The material was directly used in the next step without further characterization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-iodopyrazine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GREEN, Luke; GUBA, Wolfgang; JAESCHKE, Georg; JOLIDON, Synese; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2011/128279; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem