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, 2.3 mmol) in chlorobenzene (10 mL) was treated with a 0.69 M THF solution of 3-methyl-4-methoxyphenylmagnesium bromide (11 mL, 7.6 mmol) (prepared from 4-bromo-2-methylanisole, catalytic iodine, and magnesium turnings in THF) to provide, after chromatography (silica gel, 5-10% MeOH in CH2Cl2) 810 mg (69%) of the title compound as a yellow oil: 1H NMR d 1.43 (m, 2H), 1.58 (m, 4H), 2.11 (s, 3H), 2.46 (m, 4H), 2.71 (t, J=5.8 Hz, 2H), 3.75 (s, 3H), 3.86 (s, 3H), 4.06 (t, J=5.8 Hz, 2H), 6.64 (d, J=8.9 Hz, 1H), 6.75 (d, J=8.6 Hz, 2H), 6.95 (d, J=8.9 Hz, 1H), 7.20 (s, 2H), 7.31 (s, 1H), 7.54 (d, J=8.9 Hz, 1H), 7.77 (d, J=8.6 Hz, 2H); 13C NMR d 16.4, 24.4, 26.1, 55.3, 55.6, 55.9, 57.9, 66.4, 104.8, 110.2, 114.5, 115.0, 124.3, 125.8, 127.1, 128.0, 130.6, 130.8, 131.6, 132.5, 134.3, 140.3, 143.2, 157.9, 158.3, 163.2, 193.6; MS (FD) m/e 515 (M+); Anal. calc'd. for C31H33NO4S: C, 72.21; H, 6.45; N, 2.72. Found: C, 72.43; H, 6.53; N, 2.95.
