Methanol → HCID 15429201, compound

Participants

Reaction Steps

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.0 g, 2.29 mmol) in chlorobenzene (10 mL) was treated with a 0.64 M THF solution of 3-methoxyphenylmagnesium bromide (11.0 mL, 7.04 mmol) (prepared from 3-bromoanisole, catalytic iodide, and magnesium turnings in THF) to provide after chromatography (silica gel, 5-10% MeOH in CH2Cl2) 610 mg (53%) of the title compound as a dark oil: 1H NMR d 1.44 (m, 2H), 1.59 (m, 4H), 2.47 (m, 4H), 2.73 (t, J=6.0 Hz, 2H), 3.70 (s, 3H), 3.88 (s, 3H), 4.08 (t, J=6.0 Hz, 2H), 6.76 (m, 3H), 6.96-7.04 (m, 3H), 7.15 (t, J=8.0 Hz, 1H), 7.33 (d, J=2.0 Hz, 1H), 7.56 (d, J=8.9 Hz, 1H), 7.78 (d, J=8.7 Hz, 2H); MS (FD) m/e 501 (M+); Anal. calc'd. for C30H31NO4S: C, 71.83; H, 6.23; N, 2.79. Found: C, 71.68; H, 6.25; N, 2.66.

Provenance & Evidence