The reaction of various substituted 2,4-dichloroquinolines with 3-[1H-indol-3-yl (4-hydroxyphenyl) methyl]-1H-indole has been carried out leading to novel 4-(4-(di(1H-indol-3-yl) methyl) phenoxy)-2-chloroquinolines with high regioselectivity. All the synthesized compounds were characterized through spectral data and preliminarily evaluated for their in vitro antibacterial activity against various Gram-positive and Gram-negative organisms.