3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 6'-(3-Chloro-4-fluorophenyl)-5-methyl-2'',3'',5'',6''-tetrahydro-3'H-dispiro[imidazole-2,1 indene-2',4''-pyran]-4-amine

Participants

Reaction Steps

The title compound was synthesized as described for Example 26a in 42% yield, starting from 6′-bromo-5-methyl-2″,3″,5″,6″-tetrahydro-3′H-dispiro[imidazole-2,1′-indene-2′,4″-pyran]-4-amine (Example 25, 75 mg, 0.22 mmol) and 3-chloro-4-fluorobenzeneboronic acid (45.1 mg, 0.26 mmol); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.72 (dd, 1 H), 7.52 (m, 2 H), 7.42 (m, 2 H), 6.80 (d, 1 H), 6.60 (br. s, 1 H), 3.66 (m, 2 H), 3.48 (t, 1 H), 3.40 (m, 1 H), 3.20 (m, 1 H), 3.07 (m, 1 H), 2.19 (s, 3 H), 1.71 (td, 1 H), 1.23 (m, 3 H); MS (ES+) m/z 398 [M+H]+.

Provenance & Evidence