Methyl iodide → HCID 57752618, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-1-{3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-benzofuran-7-yl}-ethanol (0.19 g, 0.50 mmol) in THF (5 mL) is cooled to 0° C., treated with 60% NaH (23 mg, 0.56 mmol). The mixture is stirred at 0° C. for 30 min. CH3I (47 uL, 0.76 mmol) is added and the resulting mixture is stirred at 0° C. for 1 h and gradually warmed to rt. and stirred at rt overnight. The excess reagent is removed in vacuo. The residue is taked up with H2O (20 mL) and EtOAc (50 mL). It is washed with sat. NH4Cl (2×30 mL). The organic lay is dried with Na2SO4, filtered and concentrated. Purification of the crude material by chromatography gives the title compound (0.17 g, 0.41 mmol, 82%). 1H NMR (CDCl3): δ. 0.90 (t, J=7.5 Hz, 3H), 0.90 (t, J=7.5 Hz, 3H), 1.63 (d, J=4.0 Hz, 1.5H), 1.64 (d, J=4.0 Hz, 1.5H), 1.78-1.92 (m, 4H), 2.44 (s, 3H), 2.46 (s, 3H), 2.48 (s, 3H), 3.34-3.42 (m, 1H), 4.90-4.98 (m, 1H), 6.68 (s, 1H), 7.17-7.19 (m, 1H), 7.26-7.29 (m, 2H) ppm. ES-MS (m/z): calcd for C25H31N3O2 (M+H)+: 406.5. found: 406.2.

Provenance & Evidence