Quinoline → HCID 9927236, compound

Participants

Reaction Steps

To a solution of Quinoline 1 (1.0 eq.) in Et2O (0.1M) at −78° C. was added dropwise sec-BuLi (1.0 eq.). The mixture was stirred for 15 min then tri-isopropyl boronate (1.1 eq.) was added. The final mixture was warm to rt and concentrated. To the residue was added 3-bromo-1,1′ biphenyl (1.5 eq.), Na2CO3 (2M in H2O; 3.5 eq.) and Pd(PPh3)4 (0.0 Seq.) in Tol:EtOH (1:1, 0.2M). The mixture was stirred at 80° C. for 12 h, cooled to rt, poured in saturated aqueous NH4Cl 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) afforded the title compound as an oil. 1H NMR (400 MHz, acetone-d6): δ 8.82 (dd, 1H), 8.32 (dd, 1H), 7.99 (t, 1H), 7.81 (m, 2H), 7.75–7.66 (m, 4H), 7.55 (t, 1H), 7.5–7.45 (m, 3H), 7.36 (t, 1H), 3.21 (m, 1H), 1.39 (d, 6H).

Provenance & Evidence