Diiodomethane → HCID 11952183, compound

Participants

Reaction Steps

tert-Butyl nitrite (2.5 mL, 18.6 mmol) was added a stirred mixture of amine 94 (1.30 g, 6.0 mmol), diiodomethane (4.8 mL, 60 mmol) and CuI (1.2 g, 6.3 mmol) in THF (50 mL) and the mixture stirred at reflux temperature for 3 h. The solution was cooled and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (20-50%) of EtOAc/pet. ether, to give chloride 100 (1.31 g, 67%) as a pale yellow solid: mp (EtOAc/pet. ether) 140-142° C.; 1H NMR δ 8.15 (s, 1H, H-9), 7.70 (s, 1H, H-5), 3.20-3.30 (m, 2H, CH2), 2.65-2.79 (m, 3H, H-7, CH2), 1.20 (d, J=6.4 Hz, 3H, CH3); 13C NMR δ 155.5, 149.9, 147.6, 133.4, 122.5, 121.7, 114.6, 41.3, 41.0, 35.0, 20.2. Anal. calcd for C11H10IN3O: C, 40.4; H, 3.1; N, 12.9. Found: C, 40.6; H, 3.0; N, 12.7%.

Provenance & Evidence