tert-butyl Methyl(5-nitropyridin-2-yl)carbaMate synthesis

Yield:1039055-45-2 99%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide at 0; for 2.33333 h;

Steps:

101

To 0.378 g (1.58 mmol) of the above nitro compound in DMF (6 mL) at 0° C. was added 0.067 g (2.80 mmol) of sodium hydride. After 20 min, 0.12 mL (1.93 mmol) of methyl iodide was added, and the mixture was stirred for 2 hrs. Water was added, and the mixture was extracted with EtOAc (×4). The combined organic layer was washed successively with 1M HCl, sat. NaHCO₃ solution, and brine, dried (Na₂SO₄), and concentrated, to give 0.40 g (99% yield) of tert-butyl methyl(5-nitro-2-pyridinyl)carbamate: ¹H NMR (CDCl₃) δ 9.19 (d, J=2.7 Hz, 1H), 8.36 (dd, J=9.4, 2.7 Hz, 1H), 8.14 (dd, J=9.4, 0.3 Hz, 1H), 3.50 (s, 3H), 1.57 (s, 9H); LCMS (APCI^-) m/z: 253 (MH⁺, 100%).

References:

US2010/249099,2010,A1 Location in patent:Page/Page column 97