Patent ID: 7816536
Filing Date: 2010-10-19
Classification: C07D

Abstract:
1. A method for making a 4-substituted indole, benzofuran, benzothiophene, benzimidazole, benzoxazole, or benzothiazole, said method comprising: providing a 4-substituted-6,7-dihydro indole, benzofuran, benzothiophene, benzimidazole, benzoxazole, or benzothiazole compound having the formula: wherein Q 11 is a leaving group; wherein X 1 is N-Q 12 , O, or S; wherein Q 12 is an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group; wherein X 2 is C—R 3 or N; wherein R 11 is selected from a hydrogen atom, a halogen atom, an alkyl group an aryl group, a carboxylic ester group, an amide group, a aldehyde group, an alkylcarbonyl group, an arylcarbonyl group an alkyloxycarbonyl group, or an aryloxycarbonyl group, an unsubstituted, monosubstitued, or disubstituted amine, an alkoxy group, an alkylthio group, an arylthio group, and a nitro group; and wherein R 12 and R 3 are independently selected from a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a carboxylic ester group, an amide group, a aldehyde group, an alkylcarbonyl group, an arylcarbonyl group, an alkyloxycarbonyl group, or an aryloxycarbonyl group, an unsubstituted, monosubstitued, or disubstituted amine, an alkoxy group, an alkylthio group, an arylthio group, and a nitro group, or wherein R 12 and R 3 , taken together with the carbon atoms to which they are bonded, form a 5-12 membered ring; providing a diazovinyl compound having the formula: wherein Q 13 is an alkyl group or an aryl group, and wherein Q 14 is a hydrogen atom, an alkyl group, or an aryl group; or wherein Q 13 and Q 14 , taken together with the carbon atoms to which they are bonded, form a 5-12 membered ring (e.g., a substituted or unsubstituted cyclopentene or cyclohexene ring); and wherein Y is an electron withdrawing group; and contacting the 4-substituted-6,7-dihydro indole, benzofuran, benzothiophene, benzimidazole, benzoxazole, or benzothiazole compound with the vinyldiazo compound in the presence of a dirhodium catalyst under conditions effective to produce a compound having the formula: