Cesium carbonate → HCID 86603572, compound

Participants

Reaction Steps

A mixture of 1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (356 mg, 0.931 mmol), prepared in step 1 of Example 3, methyl bromoacetate (106 μL, 1.12 mmol) and cesium carbonate (457 mg, 1.40 mmol) in 25 mL of acetone was stirred under nitrogen at room temperature for 19 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted multiple times with methylene chloride. The combined organic extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give methyl {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetate (401 mg, 95%) as an off-white solid, mp 156-159° C. Elemental Analysis for C22H16BrNO3S Calc'd: C, 58.16; H, 3.55; N, 3.08. Found: C, 57.87; H, 3.43; N, 2.94.

Provenance & Evidence