Category: 1209459-10-8

These common heterocyclic compound, 1209459-10-8, name is 2-Bromo-5-fluoropyrazine, 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. Formula: C4H2BrFN2

Zinc dust (Aldrich, 325 mesh, 263 mg, 4.05 mmol) was stirred and heated in tetrahydrofuran (5 mL) with 1,2-dibromoethane (Aldrich, 68 mg, 0.364 mmol) at 65 C. under N2 for approximately 5 min. The mixture was cooled to ambient temperature. Chlorotrimethylsilane (Aldrich, 39 mg, 0.364 mmol) was then added. This mixture was allowed to stir under N2 at ambient temperature for approximately 30 min. The iodide from Part E (1.36 g, 3.0 mmol) was added, and the resulting mixture was stirred at 40 C. under N2 for approximately 3 hr. The product from Part C (0.7 g, 2.28 mmol), N,N-Dimethylacetamide (14 mL), and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (Aldrich, 93 mg, 0.114 mmol) were added to the mixture. It was stirred overnight at 80 C. under N2. The mixture was cooled to ambient temperature. Saturated aqueous NH4Cl (10 mL) was then added. The resulting mixture was diluted further with dH2O (50 mL) and ethyl acetate (100 mL), and then filtered through a bed of Celite . The layers were separated, and the aqueous layer was back-extracted with ethyl acetate (50 mL). The combined organic layers were washed with 1/1 dH2O/saturated aqueous NaCl and saturated aqueous NaCl (50 mL each), dried over MgSO4, filtered, and concentrated in vacuo to produce an oil that was purified by chromatography (silica, ethyl acetate/hexanes) to produce 90 mg (7%) of product.

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

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

Electric Literature of 1209459-10-8, The chemical industry reduces the impact on the environment during synthesis 1209459-10-8, name is 2-Bromo-5-fluoropyrazine, I believe this compound will play a more active role in future production and life.

Step 2: 2-(4-cyclopropyl-1H-imidazol-1-yl)-9-(5-fluoropyrazin-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one A suspension of 2-(4-cyclopropyl-1H-imidazol-1-yl)-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (100 mg, 0.225 mmol), 2-bromo-5-fluoropyrazine (90 mg, 0.51 mmol) and Pd(PPh3)4 (39 mg, 0.034 mmol) in DME (2.8 mL) was treated with a 2M aq. solution of Na2CO3 (0.6 mL, 1.12 mmol). The mixture was heated to 90 C. for 2 h, allowed to cool to RT and poured onto H2O. The mixture was extracted with DCM and the combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: 25% EtOAc in heptane for 2 min, then from 25% EtOAc in heptane to 100% EtOAc in heptane in 10 min, 100% EtOAc in heptane for 5 min) to yield a solid which was crystallized from diethyl ether and afforded the title compound (57 mg). UPLC-MS: MS 415.2 (M-FH+); UPLC rt 0.92 min. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.59-0.69 (m, 2H), 0.72-0.82 (m, 2H), 1.75-1.86 (m, 1H), 2.97 (t, J=5.62 Hz, 2H), 3.70 (t, J=6.11 Hz, 2H), 4.24 (br. s., 2H), 7.15 (s, 1H), 7.43 (s, 1H), 7.54 (t, J=7.82 Hz, 1H), 7.69 (d, J=7.58 Hz, 1H), 8.01-8.16 (m, 2H), 8.58 (s, 1H), 8.83 (d, J=8.31 Hz, 1H). Following the procedure described above for Example 139 and substituting the appropriate reagents, starting materials and purification methods known to those skilled in the art, the following compounds of the present invention were prepared:

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

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; US2014/57902; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1209459-10-8, name is 2-Bromo-5-fluoropyrazine, 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 1209459-10-8, COA of Formula: C4H2BrFN2

(R)-N-(6-(1-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (97 mg, 0.185 mmol), 2-bromo-5-fluoropyrazine (49.2 mg, 0.278 mmol), RuPhos (17.29 mg, 0.037 mmol), Pd(dba)2 (10.65 mg, 0.019 mmol) and Cs2CO3 (121 mg, 0.370 mmol) were combined in a vial. Toluene (0.842 ml) was added and the mixture was evacuated and back-filled with N2 three times. Heated under N2 at 80 C. overnight. The reaction was filtered through celite, rinsing with EtOAc. The filtrate was concentrated to give an orange gum. The crude sample was treated with conc. HCl/MeOH (1:10, 3 mL) at rt until the TBS group was cleaved. After concentration, the crude sample was purified by preparative HPLC (10% ACN/water to 90% ACN/water in ?40 min with 0.1% FA buffer) to give (R)-2-(5-fluoropyrazine-2-yl)-N-(6-(1-(1-hydroxypropan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (6 mg, 0.012 mmol, 6% yield).

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

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Granger, Brett; Wang, Guoqiang; Shen, Ruichao; He, Jing; He, Yong; Xing, Xuechao; Ma, Jun; Long, Jiang; Wang, Bin; Or, Yat Sun; (121 pag.)US2020/157095; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1209459-10-8, 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. 1209459-10-8, name is 2-Bromo-5-fluoropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A suspension of 2-(4- cyclopropyl-1 H-imidazol-1-yl)-9-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-7,8-dihydro- [1 ,4]diazepino[7,1-a]isoquinolin-5(4H)-one (100 mg, 0.225 mmol), 2-bromo-5-fluoropyrazine (90 mg, 0.51 mmol) and Pd(PPh3)4 (39 mg, 0.034 mmol) in DME (2.8 mL) was treated with a 2M aq. solution of Na2C03 (0.6 mL, 1.12 mmol). The mixture was heated to 90 C for 2h, allowed to cool to RT and poured onto H20. The mixture was extracted with DCM and the combined org. layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: 25% EtOAc in heptane for 2 min, then from 25% EtOAc in heptane to 100% EtOAc in heptane in 10 min, 100% EtOAc in heptane for 5 min) to yield a solid which was crystallized from diethyl ether and afforded the title compound (57 mg). UPLC-MS: MS 415.2 (M+H+); UPLC rt 0.92 min. 1H NMR (400 MHz, DMSO-d6) 8 ppm 0.59 – 0.69 (m, 2 H), 0.72 – 0.82 (m, 2 H), 1.75 – 1.86 (m, 1 H), 2.97 (t, J=5.62 Hz, 2 H), 3.70 (t, J=6.1 1 Hz, 2 H), 4.24 (br. s., 2 H), 7.15 (s, 1 H), 7.43 (s, 1 H), 7.54 (t, J=7.82 Hz, 1 H), 7.69 (d, J=7.58 Hz, 1 H), 8.01 – 8.16 (m, 2 H), 8.58 (s, 1 H), 8.83 (d, J=8.31 Hz, 1 H).

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

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem