Diiodomethane → HCID 25139486, compound

Participants

Reaction Conditions

Reaction Steps

tert-BuNO2 (90%, 3.8 mL, 28.8 mmol) was added to a stirred solution of 1-oxide 204 (2.0 g, 9.8 mmol), CH2I2 (3.8 mL, 46.7 mmol) and CuI (1.87 g, 9.8 mmol) in THF (40 mL), and the mixture was stirred at reflux temperature for 7 h. The mixture was cooled to 20° C., the solvent was evaporated and the residue purified by chromatography, eluting with a gradient (2-10%) of MeOH/DCM, to give iodide 213 (1.50 g, 49%) as a pale yellow solid: mp 192-194° C.; 1H NMR δ 8.19 (t, J=1.6 Hz, 1H, H-9), 7.10 (s, 1H, H-5), 4.83 (t, J=8.4 Hz, 2H, H-7), 3.44 (dt, J=8.4, 1.6 Hz, 2H, H-8); 13C NMR δ 167.0, 150.4, 136.2, 123.3, 116.4, 105.8, 103.7, 73.4, 29.0; HRMS calcd for C9H6IN3O2(M+) m/z 314.9505, found 314.9501.

Provenance & Evidence