Sodium hydride → HCID 66955654, compound

Participants

Reaction Steps

Alkylation of oxazine alcohol 149 (see Example 2OO) with 3-iodobenzyl bromide (1.6 equiv.) and NaH (1.8 equiv.) as in Example 2UU above for 3.5 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 0-2% EtOAc/CH2Cl2, gave 7-{[(3-iodobenzyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (155) (69%) as a cream solid: mp (CH2Cl2/pentane) 122-125° C. (dec); 1H NMR (CDCl3) δ 7.63 (br d, J=7.9 Hz, 1H), 7.58 (m, 1H), 7.40 (s, 1H), 7.19 (br d, J=7.7 Hz, 1H), 7.06 (t, J=7.7 Hz, 1H), 4.49 (s, 2H), 4.11 (ddd, J=12.4, 7.3, 5.8 Hz, 1H), 4.01 (ddd, J=12.5, 6.7, 6.0 Hz, 1H), 3.63 (d, J=10.2 Hz, 1H), 3.60 (d, J=10.2 Hz, 1H), 2.37 (ddd, J=14.4, 6.7, 6.0 Hz, 1H), 2.12 (ddd, J=14.4, 7.3, 6.0 Hz, 1H), 1.47 (s, 3H). Anal. (C15H16IN3O4) C, H, N.

Provenance & Evidence