The derivatives of Indole show biological activities including herbicidal. The newly synthesized compounds 1- phenylethyl,2-methyl,3-ethoxy carbonyl,5-methoxycarbonyl ,2- methoxy Indole (Compound 2) were prepared by treating 1- phenyl,3-ethoxycarbonyl,5-hydroxy,2-methyl Indole (Com-pound 1) successively with methyl bromo- acetate and refluxing with K2CO3 / KI in the presence of dry acetone. Newly synthesized compound 2 refluxed with hydrazine hydrate in alcoholic media forming 1-Phenylethyl,3-ethoxy carbonyl,2-methyl Indole,5-yl oxy acetic acid hydrizide (Compound 3). This drug which on separately reacting with carbon disulphide, phenyl iso-thiocynide, acetylacetone, triethylorthoformate gave condensed bridge head heterocyclic’s such as 1-Phenyl ethyl,2-methyl,3-ethoxy cabonyl,5(5’-mercapto,1’-3’-4’-oxadiazol,2’-yl )-methoxy Indole (Compound 4).