Sodium hydride → 3-Bromo-5-(((2-(1,1-dimethylethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)pyridine

Participants

Reaction Conditions

Reaction Steps

A dry round bottom flask containing 3-bromo-5-hydroxypyridine (0.1304 g, 0.749 mmol) (commercially available from Aldrich) in dry DMF (2 mL) was cooled in an ice bath. After 10 minutes, sodium hydride (0.0361 g, 0.903 mmol) (60% wt in oil) was added carefully, and the mixture was stirred at 0° C. After 10 minutes, 8.10 (0.2301 g, 0.750 mmol) was added. The reaction was allowed to stir overnight at room temperature. After 18 hours, the reaction was diluted with water and then extracted five times with EtOAc. The combined organic layers wee then washed one time with brine and dried over anhydrous magnesium sulfate. The solid was filtered off, and the solvent was concentrated. The residue was purified by silica gel flash chromatography (0-25% EtOAc/hexane) to afford 96.A (203.4 mg, 61% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.36 (2H, dd, J=13.1, 2.2 Hz), 7.62 (1H, d, J=1.6 Hz), 7.57 (1H, m), 7.29 (1H, dd, J=7.6, 1.8 Hz), 7.10 (1H, d, J=7.4 Hz), 7.02 (1H, t, J=8.8 Hz), 6.95 (2H, m), 5.14 (2H, s), 3.80 (3H, s), 1.27 (9H, s).

Provenance & Evidence