3-Aminopyridine → 8-bromo-N-(pyridin-3-yl)quinolin-2-amine

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Reaction Steps

This compound (1.03 g, 57% yield) as a tan crystalline solid was prepared similarly to that described in the preparation of 165c, using 8-bromo-2-chloroquinoline (Biofine International, Vancouver, BC; 1.46 g, 6.02 mmol), pyridin-3-amine (Aldrich; 0.68 g, 7.22 mmol), and LiHMDS (1.0 M solution in THF; 15.05 mL, 15.05 mmol) as starting materials. 1H NMR (400 MHz, DMSO-D6) δ ppm 9.93 (1H, s), 9.20 (1H, d, J=2.3 Hz), 8.84 (1H, d, J=8.4 Hz), 8.24-8.13 (2H, m), 7.99 (1H, d, J=7.6 Hz), 7.82 (1H, d, J=7.6 Hz), 7.39 (1H, dd, J=8.4, 4.7 Hz), 7.26 (1H, t, J=7.7 Hz), 7.18 (1H, d, J=8.8 Hz). m/z (ESI, +ve) 300/302 (M+H)+.

Provenance & Evidence