Category: 622392-04-5

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. Quality Control of 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

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., Formula: C4H2BrIN2

Step 1: N-1-(5-Iodo-pyrazin-2-yl)-2-methyl-propane-1,2-diamine To a solution of 2-bromo-5-iodopyrazine (CAS 622392-04-5) (250 mg, 878 mmol) in 0.7 ml of pyridine, was added 2-methylpropane-1,2-diamine (116 mg, 138 mul, 1.32 mmol, 1.5 equiv.) at room temperature. The colorless solution was stirred for 16 hours at 100 C. The reaction mixture was cooled and concentrated in vacuo. The crude material was used directly in the next step.

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; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. Safety of 2-Bromo-5-iodopyrazine

t-butyl 4-(hydroxymethyl)piperidin-1-carboxylate (the product of synthesis step 1 of compound 431; 2.70 g, 12.54 mmol), 2-bromo-5-iodopyrazine (3.57 g, 12.54 mmol) and NaH (0.36 g, 15.05 mmol) were dissolved in 70 C. for THF (30 mL), following with stirring at the same temperature for 6 hours. The reaction mixture was added with water, and extracted with EtOAc. The organic layer was washed with saturated NH4Cl aqueous solution, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography (SiO2, 12 g cartridge; EtOAchexane=0% to 20%), and concentrated to yield the title compound as white solid (4.04 g, 76%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 622392-04-5, its application will become more common.

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

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

These common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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. Recommanded Product: 2-Bromo-5-iodopyrazine

2-Bromo-5-iodopyrazine [CAS RN: 622392-04-5] (3.50 g, 12.3 mmol, 1.0 eq),4,4,5,5-tetramethyl-2-(prop-1 -en-2-yl)-1 ,3,2-dioxaborolane [CAS RN: 126726-62-3] (3.10 g, 18.4 mmo[, 1.5 eq), Pd(dppf)C[2.CH2C[2 (502 mg, 0.61 mmo[, 0.05 eq) and cesium carbonate (12.0 g, 36.9 mmo[, 3.0 eq) were dissolved in 130 mL dioxane/water (5/1). The reaction mixture was heated to 90C for 2 h. On cooling, the reaction mixture was partitioned between water anddichloromethane. The organic phase was washed with brine and the phases were separated by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 100 g SNAP cartridge: hexane -> hexane/ethyl acetate 9/1) to give 600 mg (25% yield of theory) of the title compound in a round 50% purity(UPLC-area%). The impurity was identified as 2,5-di(prop-1-en-2-yl)pyrazine, that was not expected to interfere in the subsequent reaction step. The material obtained was used without further purification.UPLC-MS (Method 4): R = 1.18 mm; MS (ESI0): m/z = 199 [M].

The synthetic route of 2-Bromo-5-iodopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (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., name: 2-Bromo-5-iodopyrazine

Into a 20-L 4-necked round-bottom flask was placed a solution of TEA (682.5 g, 6.74 mol) in 1, 4-dioxane (8.5 L) , dibromozinc (374.5 g, 1.69 mol) , tetrakis (triphenylphosphane) palladium (82.5 g, 71.39 mmol) , ethyl prop-2-ynoate (345 g, 3.52 mol) , and a solution of 2-bromo-5-iodopyrazine (400 g, 1.40 mol) in 1, 4-Dioxane (500 mL) . The resulting mixture was stirred for 10 min at 80 C, then diluted with 30 L of water/ice, and extracted with 2 x 10 L of ethyl acetate. The combined organic layers were dried in an oven under reduced pressure and concentrated under vacuum. The resulting residue was purified on a silica gel column with ethyl acetate/petroleum ether (1: 30) to provide the title compound.

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 622392-04-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEBENHAM, John S.; COX, Jason M.; LAN, Ping; SUN, Zhongxiang; FENG, Zhe; SUN, Chunrui; SEGANISH, W. Michael; LAI, Zhong; ZHU, Chen; BARA, Thomas; RAJAGOPANALAN, Murali; DANG, Qun; KIM, Hyunjin M.; HU, Bin; HAO, Jinglai; (112 pag.)WO2018/107415; (2018); 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.

Tert-butyl 4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1-(2H)-yl]sulfonyl}tetrahydro-2H-pyran-4-carboxylate (10 g, 21.86 mmol, Gateway Chemical), 2-bromo-5-iodopyrazine (6.23 g, 21.86 mmol, Gateway Chemical), toluene (105 mL), ethanol (32 mL), 2M Na2CO3(aq) (64 mL), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with CH2Cl2 (1:1) (0.892 g, 1.1 mmol, Aldrich) were heated together under N2 at 73 C. for 3 hr and then cooled to ambient temperature overnight. The resulting mixture was diluted with ethyl acetate (300 mL) and deionized water (200 mL). The layers were separated, and the aqueous was back-extracted with ethyl acetate (100 mL). The combined ethyl acetate layers were washed with 150 mL each of sat. NaHCO3(aq) and brine, dried over MgSO4, filtered, and concentrated to afford an oil in vacuo. The oil was purified by chromatography on silica (heaxnes/ethyl acetate) to afford 7.68 g (72% yield) of solids.

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; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. category: Pyrazines

Step 1: 1-(5-Bromo-pyrazin-2-yl)-4,4-dimethyl-pyrrolidin-2-one To a well stirred suspension of 2-bromo-5-iodopyrazine (300 mg, 1.05 mmol), 4,4-dimethylpiperidin-2-one (155 mg, 1.37 mmol, 1.3 equiv.) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (24.4 mg, 0.042 mmol, 0.04 equiv.) in 4 ml of toluene were added under argon atmosphere tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), (19.3 mg, 0.021 mmol, 0.02 equiv.) and the mixture was stirred for 5 hours at 100 C. The crude mixture was adsorbed on silicagel and purified by flash chromatography over a 20 g silicagel column using a 2:1 heptane/ethyl acetate mixture as eluant. The title compound (151 mg, 53% yield) was obtained as a white solid, MS: m/e=270.1, 272.1 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 622392-04-5, its application will become more common.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); 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., HPLC of Formula: C4H2BrIN2

EXAMPLE 50A (exo)-3-(5-Iodo-pyrazin-2-yloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane Under N2, the mixture of product from 7C (0.42 g, 3.0 mmol) was treated with potassium t-butoxide (Aldrich, 0.32 g, 3.3 mmol) in THF (anhydrous, Aldrich, 50 mL) at ambient temperature for 1 hours. The product of Example 41B (1.00 g, 3.5 mmol) and was added. The 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. 0.40) to provide the title compound. 1H NMR (300 MHz, CD3OD) delta 1.90-2.25 (m, 4H), 2.31-2.60 (m, 4H), 2.84 (s, 3H), 3.94-4.11 (m, 2H), 5.32-5.57 (m, 1H), 8.06 (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

Application 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.

2-bromo-5-iodopyrazine (503 mg, 1.77 mmol) and tert-butyl piperazine-1-carboxylate (355 mg, 1.91 mmol) were taken up in tBuOH (8 mL). iPr2NEt (400 muL, 2.3 mmol) was added and the stirred reaction mixture was heated to 100 C. After 66 h, the reaction mixture was cooled and was partitioned between EtOAc, water and brine. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (10-30% EtOAc in hexanes) to afford tert-butyl 4-(5-iodopyrazin-2-yl)piperazine-1-carboxylate 7.11.

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; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem