Pyrazole → HCID 90118308, compound

Participants

Reaction Steps

To a dry 2 dram vial equipped with a stir bar was added 1H-pyrazole (16 mg, 0.23 mmol), then DMF (1 mL). To the solution was added sodium hydride (60% disp. in oil, 11 mg, 0.27 mmol) upon which effervesence was immediately observed. The mixture was stirred at room temperature for 15 minutes. To the solution was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (60 mg, 0.21 mmol) as a solution in DMF (0.2 mL). The solution was stirred at room temperature for 3 hours and then at 60° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then directly purified via C18 chromatography (water:MeOH w/0.1% TFA) to afford 2-chloro-6-(4-isopropoxyphenyl)-4-(1H-pyrazol-1-yl)pyridine as an off-white solid (41 mg, 62%). 1H-NMR (400 MHz, CDCl3) δ 8.05 (d, J=2.5 Hz, 1H), 7.99 (d, J=9.0 Hz, 2H), 7.96 (d, J=1.8 Hz, 1H), 7.81 (d, J=1.5 Hz, 1H), 7.50 (d, J=1.5 Hz, 1H), 6.97 (d, J=8.8 Hz, 2H), 6.56 (dd, J=2.5, 1.8 Hz, 1H), 4.64 (dquin, J=12.2, 6.0 Hz, 1H), 1.40-1.35 (m, 6H); MS: MS m/z 314.2 (M++1).

Provenance & Evidence