HCID 10449650, compound → HCID 22716444, compound

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0) (200 mg) and cuprous bromide (20 mg) were added to a solution of 6,7-dimethoxy-2-trifluoromethanesulfonyloxy-naphthalene 10 (500 mg, 1.49 mmol) and trimethylnitroarylstannane 38 (950 mg, 2.25 mmol) in THF (40 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 for 2 days. After cooling, THF was evaporated and ethyl acetate (30 mL) was added to the residue. The solution was washed with water. The organic layer was separated and passed through a Celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4), and evaporated in vacuo. The residue was chromatographed using a 70:30 mixture of hexanes:ethyl acetate to give 39 (230 mg) in 35% yield; mp 151-153° C.; IR (KBr) 2962, 1608, 1573, 1508, 1416, 1330, 1275, 1254 cm−1; 1H NMR (CDCl3) δ3.98 (3H, s), 3.99 (3H, s), 4.01 (3H, s), 5.20 (2H. s), 6.94 (1H, s), 7.10 (1H, s), 7.14 (1H, s), 7.18 (1H, dd, J1=8.4, J2=1.8), 7.36-7.43 (5H, m), 7.54 (1H, d, J=1.5), 7.56 (1H, s), 7.68 (1H, d, J=8.3); 13C NMR δ56.37, 56.95, 71.69, 106.69, 106.99, 108.67, 116.35, 124.91, 125.78, 127.00, 128.00, 128.87, 129.00, 129.23, 129.53, 131.81, 134.49, 136.15, 141.89, 148.95, 150.41, 151.85; HRMS (EI) calcd for C26H23NO6 m/z: 445.1525; found: 445.1355.

Provenance & Evidence