Pyridine → HCID 16678748, compound

Participants

Reaction Steps

To a solution of (1H-benzimidazol-1-yl)acetic acid (1 g, 5.68 mmol) (Example 1B) in N,N-dimethylformamide (25 mL) was added thionyl chloride (0.4 mL, 5.56 mmol) drop-wise and the reaction mixture stirred at room temperature for 1 h. 6-Phenyl-pyridin-2-ylamine (5.46 mmol) and pyridine (4 mL) were then added to the reaction mixture and stirred at room temperature for 17 h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluting with 0-10% methanol in dichloromethane, affording the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 5.29 (2H, s), 7.28-7.35 (2H, m), 7.39-7.48 (3H, m), 7.54 (1H, d, J=7.2 Hz), 7.62 (1H, d, J=7.7 Hz), 7.71 (1H, d, J=7.3 Hz), 7.81 (1H, t, J=7.9 Hz), 7.98 (1H, br d), 8.05 (2H, d, J=7.3 Hz), 8.23 (1H, s). MS (ES) m/z: 329.1 [M+H].

Provenance & Evidence