(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid → 4-fluoro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide

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Reaction Steps

Example 216 was synthesized in a similar manner to Example 212, except that 1-chloro-4-fluoro-N-(4-methoxybenzyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (Intermediate QQQ) and (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (12 g silica gel column, gradient elution 25 to 100% EtOAc:Heptane) to afford 4-fluoro-1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=8.74 (s, 1H), 8.59 (d, J=17.3 Hz, 2H), 8.35-8.13 (m, 1H), 8.06 (d, J=8.9 Hz, 1H), 7.77 (d, J=9.1 Hz, 1H), 7.62-7.56 (m, 1H), 7.54-7.46 (m, 2H), 3.75 (s, 3H). m/z (ESI) 479.2 (M+H)+.

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