Ethanethiol → [2-(3-Chloro-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 4 (0.61 g, 1.14 mmol), ethanethiol (0.42 mL, 5.77 mmol), and aluminum chloride (1.07 g, 8.03 mmol) were stirred in anhydrous CH2Cl2 (20 mL). After chromatography (silica gel, 5-10% MeOH in CH2Cl2) the remnant crystallized from MeOH/CH2Cl2 to give 343 mg (59%) of the title product as a yellow solid; 1H NMR d 1.33 (m, 2H), 1.44 (m, 4H), 2.37 (m, 4H), 2.48 (s, 1H), 2.60 (t, J=5.7 Hz, 2H), 4.06 (t, J=5.7 Hz, 2H), 6.83-6.93 (m, 4H), 7.12 (dd, J=2.0 Hz, 8.5 Hz, 1H), 7.25 (m, 2H), 7.33 (d, J=2.0 Hz, 1H), 7.63 (d, J=8.7 Hz, 2H), 9.82 (br s, 1H); 13C NMR (DMSO-d6) d 23.8, 25.4, 54.2, 57.0, 65.9, 107.1, 114.5, 115.3, 116.9, 119.9, 123.5, 124.8, 128.2, 129.4, 129.5, 130.6, 131.7, 132.0, 138.5, 139.3, 153.5, 155.6, 162.9, 192.3; HRMS (FAB) m/e calc'd. for C28H27ClNO4S (MH+): 508.1349, found: 508.1344.

Provenance & Evidence