In the present study, a series of 2-aroylindole derivatives were synthesized by phase transfer catalysis (PTC) and were characterized by IR, 1H-NMR, Mass spectral and Elemental analysis. Indole derivatives 6a-g, 7a-f, 8a-f and 9a-13a were tested for analgesic activity using hot-plate test. Compounds 7b and 8b were tested for antipyretic and anti-inflammatory activity using yeast induced hyperthermia and paw edema in rats. Analgesic activity was shown when indole nucleus was substituted at position 2 and 3 by phenyl and (p-halo)benzoyl moieties respectively, where highest activity was recognised in compounds 7b and 8b. Both compounds also exhibited faster, more effective and prolonged reduction in hyperthermia and edema induced in rats compared with indomethacin. Compounds 7b and 8b were also tested for ulcerogenic activity in mice, where a lower ulcerogenic effect was observed compared with indomethacin at all tested dose levels.