Sodium Iodide → N-[1-(2-Hydroxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-1,1'-biphenyl-4-carboxamide

Participants

Reaction Steps

N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1′-biphenyl-4-carboxamide (Example 24) (100 mg, 0.304 mmol), potassium carbonate (126 mg, 0.913 mmol), sodium iodide (9 mg, 0.06 mmol) and 2-bromoethanol (216 ul, 3.04 mmol) in dioxane (1 ml) were heated at 60° C. for 8 d. After cooling to ambient temperature the reaction mixture was diluted with EtOAc (10 ml), filtered and concentrated in vacuo to give the crude product which was purified on a silica SPE column. Elution with an EtOAc/60-80° C. petroleum ether gradient gave the title compound as a beige solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.93 (d, 2H), 7.78 (s, 1H), 7.70 (d, 2H), 7.63 (d, 2H), 7.48 (t, 2H), 7.40 (t, 1H), 7.19 (d, 1H), 6.93 (d, 1H), 6.74 (dd, 1H), 3.87 (m, 2H), 3.49 (t, 2H), 3.35 (m, 2H), 2.75 (t, 2H), 1.97 (m, 3H).

Provenance & Evidence