4-Cyanophenylboronic acid → 1-(4'-cyano-1,1'-biphenyl-3-yl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide

関与物質

反応手順

A flask containing a mixture of 1-(3-bromophenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (prepared according to the general procedures described above, 80 mg, 0.20 mmol) and 4-cyanophenylboronic acid (57 mg, 0.39 mmol) was evacuated and refilled with N2 (2×). To this was added Pd(PPh3)4 (34 mg, 0.029 mmol) in one portion with minimum exposure to air. The flask was again evacuated and refilled with N2 (3×). Degassed solutions of DME-EtOH (4:1 v/v, 2 mL) and aq Na2CO3 (2M, 0.6 mL) were added via syringe and the solution was stirred under N2 for 10 min at rt and then at 85° C. for 19 h. The reaction was then cooled to rt, filtered, and purified using the Waters mass-directed HPLC purification system. Further recrystallization from acetonitrile yielded 1-(4′-cyano-1,1′-biphenyl-3-yl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide as a white solid (18.5 mg, 22% yield). MS (ES+): m/z430 (100) [MH+]. 1H NMR (400 MHz, CD3OD): δ=8.66 (s, 1H), 8.61 (d, J=2.4Hz, 1H), 8.45 (dd, J=4.8 Hz, 1.2 Hz, 1H), 8.34 (dd, J=1.0 Hz, 0.4 Hz, 1H), 7.99 (t, J=1.6 Hz, 1H), 7.88-7.86 (m, 3H), 7.86-7.82 (m, 4H), 7.80 (t, J=8.0 Hz, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.43 (dd, J=8.4 Hz, 5.2 Hz, 1H), 7.67 (s, 2H).

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