合成路线:The reaction of 3-benzyloxy-2-nitrotoluene (I) with diethyl oxalate and potassium ethoxide yields the potassium salt (II),which on reduction with iron in acetic acid atfords ethyl 7-benzyloxyindole-2-carboxylate (III).After hydrolysis of (III),7-benzyloxyindole-2 carboxylic acid (IV) is formed,which by treatment with methanolic HCl is converted to methyl 7-benzyloxyindole-2-carboxylate (V).Debenzylation of (V) with H2 over Pd/C affords methyl 7-hydroxyindole-2-carboxylate (VI).Reaction of (VI) with tert-butylaminoacetonitrile hydrochloride in the presence of AlCl3/HCl and catalytic hdrogenation of the resulting aminoketone hydrochloride (VII) over Pd/C gives ZK-90055.
参考文献标题:ZK-90055
文献作者:Loge,O.; heindl,J.; Albrecht,R.; Losert,W.
参考来源:Drugs Fut 1987,12(12),1122
合成路线:The reaction of 3-benzyloxy-2-nitrotoluene (I) with diethyl oxalate and potassium ethoxide yields the potassium salt (II),which on reduction with iron in acetic acid atfords ethyl 7-benzyloxyindole-2-carboxylate (III).After hydrolysis of (III),7-benzyloxyindole-2 carboxylic acid (IV) is formed,which by treatment with methanolic HCl is converted to methyl 7-benzyloxyindole-2-carboxylate (V).Debenzylation of (V) with H2 over Pd/C affords methyl 7-hydroxyindole-2-carboxylate (VI).Reaction of (VI) with tert-butylaminoacetonitrile hydrochloride in the presence of AlCl3/HCl and catalytic hdrogenation of the resulting aminoketone hydrochloride (VII) over Pd/C gives ZK-90055.
参考文献标题:Beta2-Agonists containing metanolically labile groups.II.The influence of ester groups in the aryl system
文献作者:Loge,O.; Heindl,J.; Albrecht,R.
参考来源:Eur J Med Chem - Chim Ther 1985,2057
产品链接: CAS No. 84638-81-3››