Electric Literature of 73112-16-0 ,Some common heterocyclic compound, 73112-16-0, molecular formula is C6H5Br2N, 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.
Preparative Example 3 – Tert-butyl (6-bromo-4-methylpyridin-2-yl)carbamate (PrepEx-3)[00186] Into a flask were added tert-butyl carbamate (5.6 g, 47.8 mmol) and 2,6-dibromo-4-methyl-pyridine (12 g, 47.8 mmol) followed by degassed 2-MeTHF (120 mL). Solid sodium tert-butoxide (4.6 g, 47.8 mmol) was then added followed bytris(dibenzylideneacetone)dipalladium(0) (1.1 g, 1.2 mmol) and l,l’-bis(di-tert- butylphosphino)ferrocene (1.1 g, 2.4 mmol), and the solution evacuated and refilled with nitrogen 3 times. The solution was heated to 70 C for 4 h and then cooled to rt. The mixture was treated with water (20 mL) and EtOAc (100 mL) and filtered through Celite. The organic solution was washed with brine (100 mL) and then concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography to afford tert-butyl (6-bromo-4- methylpyridin-2-yl)carbamate (11.2 g, 82%) as a white solid. MS ESI calcd for CnH15BrN202 [M + H]+ 287, found 287. 1H NMR (600 MHz, CDC13) delta 7.70 (s, 1H), 7.13 (s, 1H), 6.95 (s, 1H), 2.29 (s, 3H), 1.49 (s, 9H) ppm.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73112-16-0, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; ROMEO, Eric Thomas; MACHACEK, Michelle, R.; TROTTER, Benjamin Wesley; MILLER, Thomas Allen; ANDRESEN, Brian Michael; ANTHONY, Neville John; TAOKA, Brandon, M.; LIU, Yuan; WO2012/151137; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem