Reaction Steps
Following the procedure in Steps A and B of Example 14, 4-(3,4-dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl trifluoromethanesulfonate (100 mg, 0.23 mmol), 3-cyanophenylboronic acid (51 mg, 0.35 mmol), cesium carbonate (225 mg, 0.69 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (8 mg, 0.01 mmol) in N,N-dimethylformamide (2 mL) and water (1 mL) followed by N-de-methylation with N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine (52 mg, 0.24 mmol) and 1-chlorethyl chloroformate (0.08 mL, 0.72 mmol) gave 3-(4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)benzonitrile, trifluoroacetate salt (38 mg, 33%, 2 steps) as an off-white solid: 1H NMR (CD3OD, 500 MHz) δ 8.01 (d, J=1.5 Hz, 1H), 7.97-7.95 (m, 1H), 7.75-7.73 (m, 1H), 7.66-7.63 (m, 2H), 7.60 (dd, J=8.2, 1.7 Hz, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.23 (dd, J=8.3, 2.1 Hz, 1H), 7.04 (d, J=8.2 Hz, 1H), 4.65-4.52 (m, 3H), 3.83 (dd, J=12.6, 6.1 Hz, 1H), 3.51 (dd, J=12.6, 10.8 Hz, 1H); ESI MS m/z 379 [M+H]+.
