tert-Butyl carbamate → HCID 86680796, compound

Participants

Reaction Conditions

Reaction Steps

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 by tris(dibenzylideneacetone)dipalladium(0) (1.1 g, 1.2 mmol) and 1,1′-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 C11H15BrN2O2 [M+H]+ 287, found 287. 1H NMR (600 MHz, CDCl3) δ 7.70 (s, 1H), 7.13 (s, 1H), 6.95 (s, 1H), 2.29 (s, 3H), 1.49 (s, 9H) ppm.

Provenance & Evidence