Carbamic acid, N-[(6-bromo-2-pyridinyl)methyl]-N-methyl-, 1,1-dimethylethyl ester synthesis

Yield:-

Reaction Conditions:

in N,N-dimethyl-formamide at 20; for 16 h;

Steps:

105.2

A solution of l-(6-bromopyridin-2-yl)-N-methylmethanamine (300 mg, 1.49 mmol) in dimethylformamide (4.2 mL) was charged with di-tert-butyl-dicarbonate (488 mg, 2.24 mmol). The reaction mixture was maintained at ambient temperature for 16 hours and then partitioned between ethyl acetate (15 mL) and saturated aqueous sodium bicarbonate (15 mL).The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (15 mL) and brine (2 x 15 mL), dried over sodium sulfate, filtered, and concentrated.The crude product was purified by silica gel chromatography using a 5-40% ethyl acetate / hexanes gradient to afford the title compound.Calc'd for C₁₂H₁₈BrN₂O₂ [M+H]⁺: 301, Found: 301.

References:

WO2008/156726,2008,A1 Location in patent:Page/Page column 142