3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → US8865911, 46b Isomer 2

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6′-Bromo-5-methyl-5″,6″-dihydro-4″H-dispiro[imidazole-2,4′-chromene-2′,3″-pyran]-4-amine (Example 45 Isomer 1, 77 mg, 0.21 mmol) and 3-chloro-4-fluorophenylboronic acid (47.9 mg, 0.27 mmol) were reacted using the conditions described for Example 46a Isomer 1, to give Isomer 1 of the title compound (33 mg, 38% yield) with undetermined configuration: 1H NMR (500 MHz, DMSO-d6) δ ppm 1.44-1.52 (m, 1 H), 1.81-1.92 (m, 3 H), 1.97-2.05 (m, 2 H), 2.22 (s, 3 H), 3.41-3.48 (m, 1 H), 3.56 (d, 1 H), 3.67-3.74 (m, 1 H), 3.98 (d, 1 H), 6.57 (s, 2 H), 6.60 (d, 1 H), 6.94 (d, 1 H), 7.38-7.46 (m, 3 H), 7.60 (dd, 1 H); MS (ES+) m/z 414 [M+H]+.

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