3-(Benzyloxy)pyridin-2-ol → 1-(4-Azidobutyl)-3-benzyloxypyridine-2-one

Participants

Reaction Steps

Reaction of 3-benzyloxypyridine-2-one (0.40 g, 1.99 mmol) and 156c (0.58 g, 2.98 mmol) within 16 h as described for synthesis of 157a gave compound 157c (0.36 g, 62%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.22 (m, 5H), 6.78 (dd, J=6.9, 1.7 Hz, 1H), 6.54 (dd, J=7.4, 1.7 Hz, 1H), 5.91 (m, 1H), 4.96 (s, 2H), 3.85 (t, J=7.2 Hz, 2H), 3.17 (t, J=6.8 Hz, 2H), 1.71 (m, 2H), 1.48 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.52, 148.27, 135.78, 128.37, 127.98, 127.42, 126.82, 114.92, 104.32, 70.09, 50.43, 48.46, 25.83, 25.42. HRMS (EI) calcd for C16H18N4O2 [M]+ 298.1430. found 298.1446.

Provenance & Evidence