Toluene → HCID 67103012, compound

Participants

Reaction Steps

The mixture of 2,4-bis-benzyloxy-5-bromo-N-(3-methoxy-propyl)-benzamide (484 mg, 1 mmol) and 5-isopropyl-2-methoxy-phenylboronic acid (388 mg, 2 mmol) was heated in the mixture of toluene (5 ml), ethanol (5 ml) and saturated NaHCO3 (5 ml) under nitrogen in the presence of a catalytic amount of Pd(PPh3)4 (60 mg, 0.056 mmol) at 80° C. for 2-3 h. After the reaction was complete, the reaction mixture was extracted with ethyl acetate (25 ml×3), and the combined organics were washed with water and brine and dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to provide 508 mg of 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid-(3-methoxypropyl)-amide (92% yield). M.p.: 142-144 C; 400 MHz 1H NMR (CDCl3) δ: 8.16 (s, 1H), 7.92 (t, J=5.6 Hz, 1H), 7.43-7.38 (m, 5H), 7.33-7.26 (m, 5H), 7.17 (dd, J=8.4, 2.4 Hz, 1H), 7.12 (d, J=1.6 Hz, 1H), 6.87 (d, J=8.0 Hz, 1H), 6.59 (s, 1H), 5.11 (s, 2H), 5.06 (s, 2H), 3.72 (s, 3H), 3.44 (q, J=5.6 Hz, 2H), 3.30 (t, J=6.4 Hz, 2H), 3.22 (s, 3H), 2.87 (m, 1H), 1.69 (pent, J=6.4 Hz, 2H), 1.23 (d, J=6.8 Hz, 6H); LCMS: 554 [M+H].

Provenance & Evidence