Reaction Steps
A mixture of 5-(4-methoxy-phenoxy)-1H-indazole (0.20 grams, 0.83 mmol) and 1.7 mL of anhydrous dimethyl sulfoxide (previously saturated with oxygen) was treated with 3-pyridylboronic acid (0.25 grams, 1.7 mmol), copper (II) acetate (0.23 grams, 1.2 mmol), pyridine (0.34 mL, 0.33 grams, 4.2 mmol) and 4A molecular sieves (0.17 grams). After stirring for 14 days under an oxygen atmosphere, the mixture was diluted with water, extracted 3 times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexanes (0-100%), affording 5-(4-Methoxy-phenoxy)-1-pyridin-3-yl-1H-indazole (0.11 grams) (1H NMR (CDCl3, 400 MHz): δ 9.07 (d, 1H, J=2.1 Hz), 8.60 (d, 1H, J=4.2 Hz), 8.12 (s, 1H), 8.10 (dd, 1H, J=1.3, 5.8 Hz), 7.65 (dd, 1H, J=1.1, 9.6 Hz), 7.50 (dd, 1H, J=5.0, 8.3 Hz), 7.25 (m, 2H), 7.00-6.80 (m, 5H), 3.80 (s, 3H) ppm) and 5-(4-Methoxy-phenoxy)-2-pyridin-3-yl-2H-indazole (0.050 grams) (1H NMR (CDCl3, 400 MHz): δ 9.12 (bs, 1H), 8.50 (b, 1H), 8.32 (d, 1H, J=8.3 Hz), 8.29 (s, 1H), 7.73 (d\d, 1H, J=9.5 Hz), 7.54 (dd, 1H, J=4.6, 7.9 Hz), 7.16 (dd, 1H, J=2.1, 9.1 Hz), 7.01 (d, 2H, J=9.1 Hz), 6.96 (s, 1H), 6.90 (d, 2H, J=8.7 Hz), 3.81 (s, 3H) ppm) as colorless syrups.
