Some common heterocyclic compound, 1062608-42-7, name is 5-Bromo-3-iodopyrazin-2-amine, molecular formula is C4H3BrIN3, 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-Bromo-3-iodopyrazin-2-amine
To a solution of 2b (4.0 g, 13.33 mmol) in 1,4-dioxane (55 mL) was added 3- (trifluoromethyl)phenyl boronic acid (6) (2.79 g, 14.67 mmol) followed by 1M aqueous solution of potassium carbonate (26.6 mL, 26.67 mmol) at RT. Reaction mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium(II)chloride (0.65 g, 0.93 mmol) was added to the reaction mixture and was heated to reflux for 4 h, cooled to RT, filtered through celite. Filtrate was concentrated under vacuum to remove dioxane. 50 mL of water was added and extracted with dichloromethane. Organic layer combined and washed with water, dried over sodium sulfate and concentrated under vacuum. Crude product purified by flash chromatography using 30% ethyl acetate in petroleum ether to afford compound 3b (3.5 g, 83.3%) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 8.14 (s, 1H), 7.90 (d, J = 8.40 Hz, 2H), 7.84 (d, J = 8.40 Hz, 2H), 6.63 (s, 2H). LC-MS APCI: Calculated for C11H7BrF3N3: 318.10; Observed m/z [M+H]+: 318.0.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1062608-42-7, its application will become more common.
Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; UNIVERSITY OF CAPE TOWN; WATERSON, David; WITTY, Michael John; CHIBALE, Kelly; STREET, Leslie; GONZALEZ CABRERA, Diego; PAQUET, Tanya; (36 pag.)WO2017/9773; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem