(6-Bromopyridin-2-yl)-(4-methylpyridin-2-yl)amine → 4-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile

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Reaction Steps

By following essentially the same procedure in preparative example 020 and starting with 6-bromo-N-(4-methylpyridin-2-yl)pyridin-2-amine (100 mg 0.38 mmol) and 4-(5-(tributylstannyl)thiazol-2-yl)benzonitrile (328 mg, 0.69 mmol), the 4-(5-(6-(4-methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile was obtained and purified by dry flash chromatography over SiO2 eluting with EtOAc/Cyclohexane 50/50-MeOH (5%) and by trituration with Et2O (51 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ 9.77 (br s, 1H), 8.65 (s, 1H), 8.20-8.10 (m, 3H), 8.00 (d, J=8.4 Hz, 2H), 7.93 (br s, 1H), 7.75 (t, J=7.9 Hz, 1H), 7.55 (d, J=7.4 Hz, 1H), 7.50 (d, J=8.3 Hz, 1H), 6.80 (d, J=5.1 Hz, 1H), 2.39 (s, 3H). (APCI+) m/z 370 (M+H)+.

Provenance & Evidence