3-Chloro-5-cyanophenylboronic acid, pinacol ester → 3-(4''-Amino-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-7'-yl)-5-chlorobenzonitrile

Participants

Reaction Steps

The title compound was prepared following the procedure described for Example 2, starting from 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Intermediate 4, 71 mg, 0.27 mmol) and 7′-bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 1, 86 mg, 0.27 mmol). The product was purified by preparative HPLC to give the title compound (24 mg, 24% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.08 (td, 1 H), 0.10-0.16 (m, 1 H), 0.24 (ddd, 1 H), 0.49-0.62 (m, 1 H), 1.49 (dt, 1 H), 2.18 (s, 3 H), 2.32-2.44 (m, 1 H), 2.94-3.07 (m, 2 H), 6.53 (br. s, 2 H), 6.73 (d, 1 H), 7.29 (d, 1 H), 7.52 (dd, 1 H), 7.79 (t, 1 H), 7.88 (s, 1 H), 7.98 (t, 1 H); MS (ES+) m/z 375 [M+H]+.

Provenance & Evidence