Reaction Steps
A mixture of 2-(3-{3-[5-benzyloxy-2-ethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester (960 mg, 1.41 mmol), 2-bromothiazole (0.25 mL, 2.8 mmol), cesium carbonate (1.15 g, 3.52 mmol), and PdC12(dppf) (35 mg, 0.040 mmol) in de-oxygenated toluene (35 mL) was heated at 60° C. for 16 h then at 100° C. for 7 h. Additional portions of 2-bromothiazole (0.13 mL) and PdCl2(dppf) (˜30 mg) were added and heating continued at 100° C. for 72 h. The mixture was cooled to room temperature, concentrated in vacuo, diluted with methylene chloride, and filtered down a short plug of silica gel. The filtrate was concentrated in vacuo. Chromatography (silica gel, hexane to 35% ethyl acetate/65% hexane) of the residue provided 282 mg (31%) of the title compound. 1H NMR (CDCl3) δ 8.20 (s, 1H), 7.86 (dd, J=8, 1 Hz, 1H), 7.82 (d, J=3 Hz, 1H), 7.49 (d, J=7 Hz, 2H), 7.35 (m, 4H), 7.23 (d, J=3 Hz, 1H), 7.09 (d, J=9 Hz, 1H), 7.04 (d, J=9 Hz, 1H), 6.7B (d, J=9 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 6.57 (s, 1H), 6.42 (d, J=8 Hz, 1H), 5.24 (s, 2H), 4.17 (m, 4H), 3.81 (s, 3H), 2.63 (m, 4H), 2.33 (quintet, J=6 Hz, 2H), 1.55 (hextet, J=8 Hz, 2H), 1.19 (t, J=7 Hz, 3H), 0.88 (t, J=7 Hz, 3H).
