[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1.[C:11](Cl)(=[O:13])[CH3:12].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.C(N(CC)CC)C>CC#N.C(Cl)Cl>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][N:2]2[C:11](=[O:13])[CH3:12])=[CH:16]1To a solution of 3,4-dihydroisoquinoline (4.00 g, 30.5 mmol) and CH3CN (50 mL) at 0° C. was added acetyl chloride (2.13 mL, 30.5 mmol) over 2 min. The reaction was stirred 30 min and 1H-indole (3.57 g, 30.5 mmol) and triethylamine (4.25 mL, 30.5 mmol) in CH3CN (5 mL) were added and the reaction warmed to RT. The reaction was stirred under N2 3 h, then quenched with 10% HCl (100 mL), and extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with NaHCO3 (100 mL), dried (Na2SO4), and concentrated to give the crude product as a white solid (9.2 g). The solid was dissolved in CH2Cl2 (50 mL) to give a suspension which was filtered and the solid collected. The white solid (3.55 g) was recrystallized from hot acetone (230 mL) and cooled at −20° C. overnight to give 1-(1-(1H-indol-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone as a white crystalline solid.
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