Acrylonitrile → HCID 86709314, compound

Participants

Reaction Steps

A 200-mL RBF was charged with (5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (5.416 g, 15.86 mmol), tetrabutylammonium hydrogen sulfate (0.269 g, 0.793 mmol), THF (79 mL), and acrylonitrile (5.22 mL, 79 mmol) to give a clear, brown solution. NaOH (2N aq.) (19.82 mL, 39.6 mmol) was added, and the resulting biphasic mixture was stirred for 4 h. The mixture was diluted with water (110 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (100 mL), washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (0-100% EtOAc/Hexane) to afford 3-((5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methoxy)propanenitrile. 1H NMR (400 MHz, DMSO-d6) δ=8.28 (d, J=0.4 Hz, 7 H), 7.98 (s, 7 H), 7.88 (d, J=0.4 Hz, 7 H), 7.50 (dd, J=2.5, 8.7 Hz, 8 H), 7.13 (d, J=8.7 Hz, 7 H), 3.61-3.48 (m, 2 H), 3.34 (t, J=6.0 Hz, 2 H), 2.95 (s, 2 H); MS m/z=394.0. Calc'd for C16H14BrClN3O2: 394.0.

Provenance & Evidence