Sodium hydride → HCID 86650549, compound

Participants

Reaction Steps

Ring closure of alcohol 151 with NaH (1.5 equiv.) as in Example 2AA, followed by chromatography of the product on silica gel, eluting with 0-50% EtOAc/petroleum ether (foreruns) and then with 0-2% MeOH/CH2Cl2, gave 7-{[(6-bromo-3-pyridinyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (152) (66%) as a light yellow solid: mp (CH2Cl2/hexane) 170-171° C.; 1H NMR (CDCl3) δ 8.06 (dd, J=3.1, 0.3 Hz, 1H), 7.46 (s, 1H), 7.40 (dd, J=8.7, 0.3 Hz, 1H), 7.11 (dd, J=8.7, 3.2 Hz, 1H), 4.21-4.07 (m, 4H), 2.52 (ddd, J=14.5, 8.1, 6.3 Hz, 1H), 2.24 (dt, J=14.5, 5.7 Hz, 1H), 1.60 (s, 3H). Anal. (C13H13BrN4O4) C, H, N.

Provenance & Evidence