Reaction Steps
A mixture of the title compound from Step B (0.068 g, 0.13 mmol), methyl 4′-methoxy-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carboxylate (INTERMEDIATE 11) (0.075 g, 0.19 mmol), tetrakis(triphenylphosphine) palladium (15 mg, 5% mol) and sodium carbonate (0.07 g, 0.65 mmol) in 7 ml of water/EtOH/toluene (1:2:4) was heated to reflux for 5 h. TLC (EtOAc:hexane/1:3) showed that the reaction was over. The solvents were removed. Water (10 ml) was added. The organic was extracted with methylene chloride (3×20 ml). The combined methylene chloride layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after purification with preparative TLC using 10% EtOAc in hexane as the eluant. 1H NMR (CDCl3, 500 MHz): δ 1:1 mixture of atropisomers 7.96 (d, J=9 Hz, 1H), 7.88 (m, 2H), 7.72 (s, 1H), 7.65 (s, 1H), 7.49 (d, J=2 Hz, 0.5H), 7.39 (m, 2H), 7.36 (d, J=2 Hz, 0.5H), 7.24-7.28 (m, 2H), 7.15 (m, 1H), 7.70 (m, 1H), 5.62 (d, J=8 Hz, 0.5H), 5.52 (d, J=8 Hz, 0.5H), 4.91 (t, J=16 Hz, 1H), 4.08 (d, J=15.5 Hz, 0.5H), 3.95 (s, 3H), 3.88 (s, 3H), 3.87 (d, J=16 Hz, 0.5H), 3.84 (m, 1H), 2.39 (s, 1.5H), 2.33 (s, 1.5H), 0.56 (d, J=7 Hz, 1.5H), 0.43 (d, J=6.5 Hz, 1.5H).
