4-Iodo-1-tritylimidazole → HCID 67207459, compound

Participants

Reaction Steps

To a stirred solution of 4-iodo-1-trityl-1H-imidazole (300 mg, 0.688 mmol) in anhydrous THF (4 mL) at room temperature was added EtMgBr (1.0 M in THF, 0.802 mmol, 0.8 mL) dropwise, under an atmosphere of N2. The resulting solution was allowed to stir for 90 min and anhydrous ZnCl2 (109 mg, 0.802 mmol) was added. The resulting white suspension was allowed to stir for 90 min and a solution of the (2S,5R)-2-(2-iodophenethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (237 mg, 0.573 mmol) in THF (1 mL) was added followed by the immediate addition of Pd(PPh3)4 (33 mg, 0.029 mmol). The reaction mixture was allowed to stir at 70° C. for 12 h under an atmosphere of N2. After cooling to room temperature, the solution was diluted with CH2Cl2 (10 mL) and the organic layer was washed with an EDTA (aq) buffer (pH=9) (2×5 mL) and brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by flash column chromatography to afford the desired product as yellow oil (87 mg, 0.146 mmol, 29%). 1H NMR: 0.70 (d, 3H, J=6 Hz), 1.02 (d, 3H, J=7.2 Hz), 1.72-1.81 (m, 1H), 2.01-2.08 (m, 1H), 2.15-2.24 (m, 1H), 2.80-3.09 (m, 2H), 3.54 (s, 3H), 3.56 (s, 3H), 3.86-3.91 (m, 214), 6.94 (d, 1H, J=1.2 Hz), 7.15-7.22 (m, 9H), 7.27 (d, 1H, J=1.6 Hz), 7.32-7.36 (m, 8H), 7.48 (d, 1H, J=1.2 Hz), 7.58-7.61 (m, 1H).

Provenance & Evidence