3-Chloro-5-cyanophenylboronic acid, pinacol ester → US9000184, 10, isomer 1

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Reaction Steps

The title compound was prepared following the procedure described for Example 2, starting from 7′-bromo-4-methoxy-5″-methyl-3′,4′-dihydrodispiro[cyclohexane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 5, 125 mg, 0.32 mmol) and 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Intermediate 4, 93 mg, 0.35 mmol). The product was purified using preparative chromatography followed by concentration of the fractions, extraction of the remaining aqueous phase with DCM, washing the organic layer with water and concentration and drying in vacuo at 50° C. for 2 days to give:

Provenance & Evidence