Potassium Carbonate → 1-(2-Azidoethyl)-3-methoxypyridine-2-one

Participants

Reaction Steps

3-methoxypyridine-2-one (0.40 g, 3.20 mmol), 156a (0.79 g, 4.80 mmol), and K2CO3 (1.32 g, 9.60 mmol) stirred overnight in THF at reflux temperature. Reaction mixture was cooled down to room temperature. Reaction mixture was partitioned between CH2Cl2 (60 mL) and water (50 mL). Organic layer washed with water (2×35 mL), brine (1×30 mL). Organic layer dried on Na2SO4 and evaporated in vacuo. Crude product was purified by flash chromatography with stepwise gradient of CH2Cl2 and acetone (max 15%) to give 0.34 mg of 157a (55%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 6.77 (dd, J=6.9, 1.6 Hz, 1H), 6.48 (dd, J=7.5, 1.6 Hz, 1H), 5.96 (m, 1H), 3.91 (m, 2H), 3.62 (s, 3H), 3.52 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.39, 149.41, 128.61, 112.16, 104.37, 55.36, 49.00, 48.91. HRMS (EI) calcd for C8H10N4O2 [M]+ 194.0804. found 194.0816.

Provenance & Evidence