Nitrogen → HCID 66652116, compound

Participants

Reaction Steps

Using a 2 neck v shaped flask, combine 6-Methoxy-3,3-dimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (1.3 g, 4.9 mmol), and 4 bromoanisole (0.16 ml, 4.9 mmol) in dioxane (40 ml) exchange with N2 add sodium t-butoxide, Add Pd[P(C4H9)3]2 exchange with N2. Heat at 80° stirring over night. Keeping reaction under N2 quench with acetic acid (6 ml). Dilute with ethyl acetate (50 ml), wash with saturated aqueous sodium bicarbonate 3× (50 ml), with brine (40 ml), dry, and concentrate. Chromatograph residue on an biotage eluting with 0-10% ethyl acetate in hexanes to give the title compound (1.6 g, 90%): 1H NMR (CDCl3) δ 8.02-7.99 (d, 1H), 7.07-7.05 (d, 2H), 6.9-6.88 (d, 2H), 6.85-6.82 (dd, 1H), 6.69-6.68 (d, 1H), 3.88 (s, 3H), 3.81 (s, 3H), 3.17-3.12 (m, 1H), 2.68-2.62 (m, 1H), 1.68-1.60 (m, 1H), 1.52-1.44 (m, 3H), 1.41-1.37 (m, 1H), 1.30-1.24 (m, 1H), 1.18-1.13 (m, 1H), 1.1 (s, 3H), 0.99 (s, 3H).

Provenance & Evidence