ethyl 5-amino-1-benzofuran-2-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 50 ml of DMF are added to 0.95 g of Boc-sarcosine and 1.21 g of ethyl 5-aminobenzofuran-2-carboxylate. 1.77 g of TBTU and 0.23 g of HOBt are then added, and the mixture is neutralised using 4 ml of triethylamine. The mixture is stirred overnight at room temperature.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 50 ml of DMF are added to 0.95 g of Boc-sarcosine and 1.21 g of ethyl 5-aminobenzofuran-2-carboxylate. 1.77 g of TBTU and 0.23 g of HOBt are then added, and the mixture is neutralised using 4 ml of triethylamine. The mixture is stirred overnight at room temperature.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The appropriate arylcarboxylic acid is synthesized by the coupling of indole-2-carboxylic acid, benzofuran-2-carboxylic acid or benzothiophene-2-carboxylic acid with ethyl 5-amino-aryl-2-carboxylate in DMF with EDCI, and saponification of the ester. Ethyl 5-aminoindole-2-carboxylate is formed by catalytic hydrogenation of ethyl 5-nitroindole-2-carboxylate (Parmerter, S. M.; Cook, A. G.; Dixon, W. B. J. Am. Chem. Soc. 1958, 80, 4621). Ethyl 5-aminobenzothiophene-2-carboxylate can be synthesized as described in: Zambias, R. A.; Hammond, M. L. J. Syn. Commun. 1991, 21, 959. Ethyl 5-aminobenzofuran-2-carboxylate is prepared from the commercially available 5-nitrobenzofuran-2-carboxylic acid.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2.3 g of ethyl 5-nitrobenzofuran-2-carboxylate in 60 ml of methanol is hydrogenated in the presence of Raney nickel. The catalyst is filtered off and the solution is concentrated. After customary working up, ethyl 5-aminobenzofuran-2-carboxylate, Rf 0.1 (dichloromethane/ethanol 9.5:0.5) obtained; hydrochloride m.p. 246°-248°. The catalyst is filtered off the solution is concentrated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The appropriate arylcarboxylic acid is synthesized by the coupling of indole-2-carboxylic acid, benzofuran-2-carboxylic acid or benzothiophene-2-carboxylic acid with ethyl 5-amino-aryl-2-carboxylate in DMF with EDCI, and saponification of the ester. Ethyl 5-aminoindole-2-carboxylate is formed by catalytic hydrogenation of ethyl 5-nitroindole-2-carboxylate (Parmerter, S. M.; Cook, A. G.; Dixon, W. B. J. Am. Chem. Soc. 1958, 80, 4621). Ethyl 5-aminobenzothiophene-2-carboxylate can be synthesized as described in: Zambias, R. A.; Hammond, M. L. J. Syn. Commun. 1991, 21, 959. Ethyl 5-aminobenzofuran-2-carboxylate is prepared from the commercially available 5-nitrobenzofuran-2-carboxylic acid.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2.3 g of ethyl 5-nitrobenzofuran-2-carboxylate in 60 ml of methanol is hydrogenated in the presence of Raney nickel. The catalyst is filtered off and the solution is concentrated. After customary working up, ethyl 5-aminobenzofuran-2-carboxylate, Rf 0.1 (dichloromethane/ethanol 9.5:0.5) obtained; hydrochloride m.p. 246°-248°. The catalyst is filtered off the solution is concentrated