4-Iodoaniline → HCID 68546506, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-1-(2-methyl-oxiranylmethyl)-4-nitro-1H-imidazole (prepared as described by Goto, F.; et al: WO 2004035547; 0.54 g, 2 mmol), 4-iodoaniline (1.31 g, 6 mmol) and cobalt (II) chloride hexahydrate were suspended in 15 mL acetonitrile and stirred at 60° C. for 3 hours. The resulting mixture was filtered through a Celite pad and washed with EtOAc. Upon removing solvent, brown solid precipitated out. The precipitate (˜200 mg) was dried and dissolved in 5 mL DMF. The solution was cooled to −78° C. before NaH (20 mg, 60% in mineral oil) was added quickly. The resulting mixture was warmed up to room temperature and stirred for one hour, before it was quenched with 1 mL water and partitioned in 50 mL EtOAc/50 mL water. The organic layer was washed with brine and dried over Na2SO4. The concentrated residue was purified by aolumn chromatography (EtOAc/Hexanes, v/v, 1/1 to 4/1) to give the titled product (90 mg) as yellow solid. ESI MS m/z 401 (M+H). 1H NMR (400 MHz, MeCN-d3) δ 7.66 (s, 1H), 7.39 (d, J=5.2 Hz, 2H), 6.52 (d, J=5.2 Hz, 2H), 4.75-4.91 (m, 1H), 4.20 (d, J=10.4 Hz, 1H), 4.02 (d, J=10.4 Hz, 1H), 3.37-3.58 (m, 2H), 1.63 (s, 3H).

Provenance & Evidence