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