3-(Benzyloxy)pyridin-2-ol → 1-(6-Azidohexyl)-3-benzyloxypyridine-2-one

Participants

Reaction Steps

Reaction of 3-benzyloxypyridine-2-one (0.50 g, 2.49 mmol) and 156d (0.66 g, 2.98 mmol) within 16 h as described for synthesis of 157a gave compound 157e (0.48 g, 60%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.15 (m, 5H), 6.65 (dd, J=7.4, 1.8 Hz, 1H), 6.45 (dd, J=7.4, 1.8 Hz, 1H), 5.81 (t, J=7.1 Hz, 1H), 4.92 (s, 2H), 3.76 (t, J=6.8 Hz, 2H), 3.05 (t, J=6.8 Hz, 2H), 1.58 (m, 2H), 1.40 (m, 2H), 1.90 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 157.55, 148.25, 135.95, 128.60, 128.10, 126.95, 126.50, 115.05, 104.90, 70.50, 51.05, 49.20, 28.65, 28.50, 26.20, 25.80. HRMS (FAB) calcd for C18H23N4O2 [M+H]+ 327.1821. found 327.1848.

Provenance & Evidence