Hydrogen Bromide → HCID 11952365, compound

Participants

Reaction Conditions

Reaction Steps

NaNO2 (23 mg, 0.33 mmol) was added to a stirred mixture of amine 124 (77 mg, 0.33 mmol), HBr (48%, 2 mL) and DMF (2 mL) at 20° C. and the mixture stirred at 20° C. for 1 h. CuBr (57 mg, 0.40 mmol) was added and the reaction mixture stirred at 20° C. for 90 min. The mixture was diluted with EtOAc (50 mL) and washed with water (3×20 mL). The organic solution was dried and the solvent evaporated to give an orange oil, that was purified by chromatography, eluting with a gradient (0-30%) of EtOAc/pet. ether, to give bromide 125 (40 mg, 41%) as an oil: 1H NMR δ 8.19 (s, 1H, H-9), 7.74 (s, 1H, H-5), 3.72 (d, J=6.5 Hz, 2H, CH2O), 3.22-3.33 (m, 2H, CH2), 2.96-3.08 (m, 2H, CH2), 2.80-2.89 (m, 1H, CH), OH not observed; HRMS calcd for C11H1079BrN3O2 (M+) m/z 294.9956, found 294.9949; calcd for C11H1081BrN3O2 (M+) m/z 296.9936, found 296.9943.

Provenance & Evidence