Sodium hydride → HCID 86650554, compound

Participants

Reaction Steps

Ring closure of alcohol 190 with NaH (1.35 equiv.) as in Example 2GGG for 200 min, followed by chromatography of the product on silica gel, eluting with 0-1% MeOH/CH2Cl2 (foreruns) and then with 1-3% MeOH/CH2Cl2, gave 6-{[(6-bromo-3-pyridinyl)oxy]methyl}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (191) (71%) as a pale yellow solid: mp (MeOH/CH2Cl2/hexane) 197-199° C.; 1H NMR [(CD3)2SO] δ 8.15 (br d, J=3.0 Hz, 1H), 8.10 (s, 1H), 7.56 (dd, J=8.7, 0.3 Hz, 1H), 7.42 (dd, J=8.8, 3.2 Hz, 1H), 4.60 (dd, J=11.0, 2.7 Hz, 1H), 4.45 (dd, J=11.0, 7.0 Hz, 1H), 4.29 (dd, J=12.5, 5.5 Hz, 1H), 4.20 (dd, J=10.0, 6.8 Hz, 1H), 4.17 (dd, J=10.0, 6.711z, 1H), 4.05 (dd, J=12.6, 6.8 Hz, 1H), 2.85 (m, 1H). Anal. (C12H11BrN4O4) C, H, N.

Provenance & Evidence