Sodium hydride → HCID 66956553, compound

Participants

Reaction Steps

A mixture of oxazine alcohol 180 (see Example 2MMM) (200.3 mg, 1.01 mmol) and 3-iodobenzyl bromide (406 mg, 1.37 mmol) in anhydrous DMF (7.5 mL) under N2 at 0° C. was treated with 60% NaH (57 mg, 1.43 mmol), then quickly degassed and resealed under N2. After stirring at room temperature for 140 min, the mixture was cooled (CO2/acetone), quenched with ice/aqueous NaHCO3 (10 mL) and diluted with water (40 mL) to precipitate a crude solid, which was collected by filtration and washed with water and petroleum ether (0.49 g). The filtrate was extracted with EtOAc (3×80 mL), and then the extracts were washed with brine (50 mL). The combined extracts were evaporated to dryness and the residue was combined with the solid above and chromatographed on silica gel. Elution with 0-1% EtOAc/CH2Cl2 firstly gave foreruns, and then further elution with 1-2% EtOAc/CH2Cl2 gave 6-{[(3-iodobenzyl)oxy]methyl}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (182) (184 mg, 44%) as a cream solid: mp (CH2Cl2/hexane) 127-130° C.; 1H NMR (CDCl3) δ 7.69-7.62 (m, 2H), 7.40 (s, 1H), 7.24 (m, 1H), 7.10 (br t, J=8.0 Hz, 1H), 4.51 (dd, J=11.4, 3.1 Hz, 1H), 4.48 (d, J=12.3 Hz, 1H), 4.44 (d, J=12.2 Hz, 1H), 4.35 (dd, J=11.4, 7.7 Hz, 1H), 4.14 (dd, J=12.3, 5.5 Hz, 1H), 4.02 (dd, J=12.3, 7.4 Hz, 1H), 3.60 (dd, J=9.6, 5.8 Hz, 1H), 3.54 (dd, J=9.6, 6.7 Hz, 1H), 2.66 (m, 1H). Anal. (C14H14IN3O4) C, H, N.

Provenance & Evidence