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0 °C

Into a 40 mL screw-cap vial were added triphenylphosphine (1.55 g, 5.91 mmol) and toluene. The solution was stirred a 0° C. for 5 min then a diisopropylazodicarboxylate (1.18 mL, 5.99 mmol) was added drop-wise over 2 min. The solution was allowed to warm to room temperature over 1 h, then a solution of 5-bromo-2-methoxy-phenol (1.01 g, 4.98 mmol) and 1-methyl-piperidin-4-ol (701 mg, 6.08 mmol) in 4 mL of toluene was added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was adsorbed onto silica gel and purified by silica gel flash chromatography with a 0-20% MeOH/CH2Cl2 gradient to afford titled compound as a light yellow oil that solidified upon standing (906 mg, 61%). 1H NMR (MeOH-d4) 7.10 (d. J=8.8, 1H), 7.08 (dd. J=8.8, 2.4, 1H), 6.89 (d, J=8.8, 1H), 4.34 (m, 1H), 3.80 (s, 3H), 2.73 (m, 2H), 2.34 (m, 2H), 2.29 (s, 3H), 1.95 (m, 2H), 1.81 (m, 2H). LC/MS (Method B) 1.85 min, [M+1]+ 300/302.

1. customInto a 40 mL screw-cap vial
2. temperatureto warm to room temperature over 1 h
3. stirringThe reaction mixture was stirred at room temperature for 3 h
4. custompurified by silica gel flash chromatography with a 0-20% MeOH/CH2Cl2 gradient