3,4-Difluorobenzeneboronic acid → 2-(3,4-Difluoro-phenyl)-5-imidazol-1-ylmethyl-pyridine

Participants

Reaction Steps

Synthesized using 3,4-difluorophenylboronic acid (270 mg, 1.68 mmol) and 1a (200 mg, 0.84 mmol) according to Method C. Yellow solid. Yield: 210 mg, 0.77 mmol, 92%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.18 (s, 2H), 6.92 (t, J=1.3 Hz, 1H), 7.13 (t, J=1.3 Hz, 1H), 7.25 (ddd, J=9.8, 8.5, 8.2 Hz, 1H), 7.49 (dd, J=8.2, 2.5 Hz, 1H), 7.59 (s, 1H), 7.66 (dd, J=8.3, 0.6 Hz, 1H), 7.69-7.73 (m, 1H), 7.86 (ddd, J=11.4, 7.6, 2.2 Hz, 1H), 8.56 (dd, J=2.3, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.0, 116.0 (d, J=18.2 Hz), 117.6 (d, J=17.3 Hz), 119.0, 120.2, 122.8 (dd, J=3.8, 6.7 Hz), 130.4, 130.6, 135.6 (dd, J=3.8, 5.8 Hz), 135.9, 137.3, 148.6, 150.8 (dd, J=20.2, 255.3 Hz), 151.3 (dd, J=15.4, 254.3 Hz), 155.3; MS (ESI): m/z=272.10 [M+H]+.

Provenance & Evidence