1H-indol-4-ol → 6-(1H-indol-4-yloxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amine

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Using Method X with 150 mg of 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine and 4-hydroxyindole, the title compound was obtained (34 mg). Yield: 17%. 1H NMR (250 MHz, DMSO-d6) δ 3.24 (s, 6H), 3.49 (s, 3H), 6.10-6.12 (m, 1H), 6.66 (s, 2H), 6.79 (d, 1H, J=7.1 Hz), 7.07 (t, 1H, J=7.8 Hz), 7.25-7.29 (m, 2H), 7.79 (s, 1H), 7.92 (s, 1H), 9.44 (s, 1H), 11.26 (s, 1H). 13C NMR (62.9 MHz, DMSO-d6) δ 55.12, 59.96, 95.43, 98.04, 108.42, 109.87, 120.50, 120.91, 121.37, 125.36, 127.87, 131.91, 136.34, 138.13, 146.33, 150.59, 152.58, 157.84. m/z 393.1 [(M+H)+ calcd for C21H20N4O4 392.1].

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