Ethanethiol → [2-(2-Methyl-4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

Participants

Reaction Steps

By the method described in Example 2, the product of Example 15 (1.0 g, 1.94 mmol), ethanethiol (0.71 mL, 9.75 mmol), and aluminum chloride (1.81 g, 13.57 mmol) were stirred in anhydrous CH2Cl2 (40 mL). Purification by chromatography (silica gel, 5-10% MeOH in CH2Cl2), provided 260 mg (27%) of the title product as a dark yellow foam: 1H NMR d 1.47 (m, 2H), 1.61 (m, 4H), 2.13 (s, 3H), 2.55 (m, 4H), 2.77 (t, J=5.5 Hz, 2H), 4.09 (t, J=5.5 Hz, 2H), 4.87 (s, 2H), 6.45 (m, 2H), 6.77 (d, J=8.7 Hz, 2H), 6.87 (dd, J=2.2, 8.8 Hz, 1H), 7.01 (d, J=9.1 Hz, 1H), 7.23 (d, J=2.2 Hz, 1H), 7.51 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.7 Hz, 2H); MS (FD) m/e 488 (MH+); HRMS (FAB) m/e calc'd. for C29H30N1O4S1 : 488.1896, found: 488.1911.

Provenance & Evidence