Hydrochloric Acid → HCID 67996047, compound

Participants

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 1,4-dioxane (20 mL), 22 (500 mg, 3.00 mmol), 25 (630 mg, 3.01 mmol) and 1 M THF solution of lithium hexamethyldisilazide (15 mL, 5.00 mmol). After bubbling nitrogen through the resulting solution for 30 min, Xantphos (148 mg, 0.255 mmol) and tris(dibenzylidene acetone)dipalladium(0) (138 mg, 0.150 mmol) were added, and the reaction mixture was heated at reflux for 3 h. After this time, the reaction was cooled to room temperature, and water (20 mL) was added. The pH was adjusted to 7 with 1 N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with water (2×25 mL), absorbed on silica gel and purified by flash chromatography to afford an 66% yield (590 mg) of 26 as a light brown solid: mp 140-141° C. 1H NMR (500 MHz, CDCl3) δ 10.63 (s, 1H), 7.78 (s, 1H), 7.46 (s, 1H), 5.84 (s, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.23 (t, 4H, J=7.0 Hz), 2.09 (m, 2H); MS (APCI+) m/z 295.8 (M+H).

Provenance & Evidence