Dimethylamine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(dimethylamino)ethoxy)phenyl)but-1-enyl)phenol

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Reaction Steps

According to the same procedure as example 1, step E described, 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (70 mg, 1.0 eq, made by example 11, step D) was reacted with dimethylamine (1 mL) in MeOH (8 mL) under reflux to give the desired product (27 mg, 38%, Z/E=1/1.2) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.23 & 7.21 (s, 1H), 7.20 (d, J=8.8 Hz, 1H), 7.08 & 7.06 (d, J=9.2 Hz, 2H), 7.00 & 6.97 (d, J=8.4 Hz, 1H), 6.79 & 6.67 (d, J=8.6 Hz, 2H), 6.66 (d, J=8.4 Hz, 2H), 6.45 & 6.24 (d, J=8.8 Hz, 2H), 6.43 & 6.41 (s, 1H), 4.10 & 3.89 (t, J=5.2 Hz, 2H), 2.86 & 2.75 (t, J=5.2 Hz, 2H), 2.49 (q, J=7.2 Hz, 2H), 2.44 & 2.37 (s, 6H), 0.91 (t, J=7.2 Hz, 3H); m/z=462[M+1]+.

Provenance & Evidence