Potassium Phosphate, Tribasic → Methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)benzoate

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The reaction mixture of methyl 4-(trifluoromethylsulfonyloxy)-3-(1-vinylcyclopentyl)benzoate 26.4 (0.29 g, 0.8 mmol), 5-fluoro-2-methoxypyridin-4-ylboronic acid (0.2 g, 1.0 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), potassium phosphate (0.5 g, 2.0 mmol), S-phos (0.06 g, 0.2 mmol) and palladium acetate (0.02 g, 0.08 mmol) in DMF (1.5 mL) was purged with nitrogen three times. The resulting mixture was heated at 90° C. for 2 hours. After work up, the product was purified by CombiFlash® silica gel column chromatography, eluting with hexane/EtOAc 9/1, to give the compound 26.5. 1H NMR (500 MHz, CDCl3) δ ppm 8.20 (1H, d, J=1.7 Hz), 8.00 (1H, s), 7.91 (1H, dd, J=7.8, 1.7 Hz), 7.10 (1H, d, J=8.1 Hz), 6.63 (1H, d, J=4.9 Hz), 5.87 (1H, dd, J=17.4, 10.5 Hz), 4.97 (1H, d, J=10.5 Hz), 4.69 (1H, d, J=17.4 Hz), 3.98 (3H, s), 3.85 (3H, s), 2.00-2.20 (1H, m), 1.80-1.96 (1H, m), 1.51-1.75 (6H, m). MS ESI (pos.) m/e: 355.9 (M+H)+.

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