2-Chlorobenzyl chloroformate → HCID 11584392, compound

Participants

Reaction Steps

2-Chlorobenzyl chloroformate (0.011 mL, 0.070 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.021 g, 0.059 mmol; prepared as described in Example 11) in a mixture of THF (3 mL) and 2 M sodium bicarbonate aqueous solution (0.3 mL). The mixture was stirred at room temperature for 2 hours. Mixture was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.026 g (70%) of the title compound as a yellow solid. MS (ESP+) m/z 517.03 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.60 (m, 1H), 7.81 (m, 1H), 7.60 (d, 1H, J=8.2 Hz), 7.39 (m, 3H), 7.27 (m, 2H), 7.07 (dd, 1H, J=8.1, 1.8 Hz), 6.99 (d, 1H, J=1.8 Hz), 6.90 (d, 1H, J=8.1 Hz), 6.05 (s, 2H), 5.24 (s, 2H), 4.36 (m, 2H), 3.48 (m, 1H), 2.98 (m, 2H), 2.17 (m, 2H), 1.86 (m, 2H).

Provenance & Evidence