4-Cyano-2-methoxyphenylboronic acid → 1-(4-cyano-2-methoxyphenyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide

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The title compound was prepared in an analogous manner to that of EXAMPLE 228, except that 1-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide and (4-cyano-2-methoxyphenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM) to afford 1-(4-cyano-2-methoxyphenyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=8.76 (d, J=1.4 Hz, 1H), 8.50 (d, J=1.4 Hz, 1H), 8.48 (s, 1H), 8.00 (dd, J=1.7, 8.9 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.76 (s, 1H), 7.62 (dd, J=1.1, 7.7 Hz, 1H), 7.57-7.52 (m, 1H), 3.72 (s, 3H). m/z (ESI) 442.2 (M+H)+.

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