Hydrogen Peroxide → HCID 57752649, compound

Participants

Reaction Steps

A solution of 8-(1-ethyl-propyl)-3-(7-isopropenyl-2-methyl-benzo[b]thiophen-3-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.58 g, 1.45 mmol) in THF (20 mL) is cooled to −78° C., and treated with 2.0 M BH3.SMe2 (2.2 mL, 4.3 mmol). The reaction is stirred in the cooling bath, allowed to warm up gradually to RT and stirred at RT overnight. It is cooled to 0° C., treated with CH3OH (10 mL), 5 M NaOH (10 mL), and 30% H2O2 (10 mL). The resulting mixture is stirred at 0° C. for 15 ml, and then at RT for 4 h. It is diluted with H2O (100 mL); extracted with EtOAc (3×100 mL). The combined organic layers is washed with 5% Na2SO3 (100 mL), H2O (100 mL); dried with Na2SO4; filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.35 g, 0.83 mmol, 57%). 1H NMR (CDCl3): δ 0.91 (t, J=7.0 Hz, 3H), 0.92 (t, J=7.0 Hz, 3H), 1.44 (d, J=3.5 Hz, 1.5H), 1.46 (d, J=3.5 Hz, 1.5 Hz), 1.75-1.95 (m, 4H), 2.38 (s, 3H), 2.42 (s, 3H), 2.44 (s, 3H), 3.25-3.40 (m, 1H), 3.40 (bs, 1H), 3.82-4.03 (m, 2H), 6.68 (s, 1H), 7.11 (d, J=7.5 Hz, 1H), 7.19 (d, J=7.5 Hz, 1H), 7.27 (t, J=7.5 Hz, 1H) ppm. ES-MS (m/z): calcd for C25H31N3OS (M+H)+: 422.6. found: 422.3.

Provenance & Evidence