4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride) → [4-(5-Imidazol-1-ylmethyl-pyridin-2-yl)-phenyl]-diphenyl-amine

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Reaction Steps

Synthesized using 4-(diphenylamino)phenylboronic acid (364 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 140 mg, 0.34 mmol, 55%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.16, (s, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.06 (tt, J=7.3, 1.3 Hz, 2H), 7.12-7.15 (m, 7H), 7.25-7.29 (m, 4H), 7.45 (dd, J=8.2, 2.2 Hz, 1H), 7.58 (br, s, 1H), 7.65 (dd, J=8.2, 0.6 Hz, 1H), 7.83-7.86 (m, 2H), 8.54 (dd, J=2.5, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.2, 119.0, 119.8, 122.8, 123.4, 124.9, 127.7, 129.2, 129.3, 130.2, 132.0, 135.7, 137.3, 147.3, 148.5, 149.1, 157.3; MS (ESI): m/z=402.94 [M+H]+.

Provenance & Evidence