HCID 10049064, compound → HCID 10369444, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)quinolin-8-yl]-biphenyl-3-yl}-ethanone from Step 1 (1.0 eq.) in THF (0.1M) was added CeCl3 (1.1 eq.). The mixture was put in an ultrasonic bath for 15 min, cooled to −78° C. then phenyl magnesium bromide was added (5.0 eq.). The final mixture was stirred for 12 h at −20° C., poured in NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 1:9 over 20 min) afforded the title compound as a white solid. 1H NMR (400 MHz, acetone-d6): δ 8.91 (dd, 1H), 8.46 (dd, 1H), 8.29 (d, 1H), 8.18 (d, 1H), 7.97 (d, 1H), 7.86 (d, 1H), 7.68 (dd, 1H), 7.64 (dd, 1H), 7.59–7.50 (m, 5H), 7.48 (d, 1H), 7.39 (t, 1H), 7.27 (t, 2H), 7.16 (t, 1H), 4.73 (s, 1H), 2.72 (s, 3H), 1.99 (s, 6H), 1.98 (s, 3H).

Provenance & Evidence