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Methyl 5-aminothiophene-2-carboxylate Application:80073537
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methyl 5-nitrothiophene-2-carboxylate
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h; | 100% |
With hydrogen; palladium 10% on activated carbon In ethanol under 760.051 Torr; | 92% |
Stage #1: methyl 5-nitrothiophene-2-carboxylate With hydrogenchloride; tin(ll) chloride In ethanol; water at 20 - 35℃; for 2h; Stage #2: In water pH=9; basic conditions; | 66% |
methanol
2-thiophenylcarboxylic acid
A
methyl 5-aminothiophene-2-carboxylate
B
methyl 4-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: 2-thiophenylcarboxylic acid With sulfuric acid; nitric acid at 0 - 10℃; for 1.25h; Stage #2: methanol With thionyl chloride at 20℃; Reflux; | A 8.5% B 31% |
5-nitrothiophene-2-carboxylic acid
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: SOCl2 2: Fe; AcOH View Scheme | |
Multi-step reaction with 3 steps 1: thionyl chloride / 1,2-dichloro-ethane / 0.5 h / 150 °C / Microwave irradiation 2: dichloromethane / 0 - 20 °C 3: 20 % Pd(OH)2/C; hydrogen / ethanol View Scheme | |
Multi-step reaction with 2 steps 1: methanol / Reflux 2: ammonium formate; zinc / ethanol; ethyl acetate View Scheme |
methyl 5-nitrothiophene-2-carboxylate
iron
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
In methanol; water |
2-thiophenylcarboxylic acid
A
methyl 5-aminothiophene-2-carboxylate
B
methyl 4-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: 2-thiophenylcarboxylic acid With sulfuric acid; nitric acid at 0 - 10℃; Stage #2: With methanol; thionyl chloride at 20℃; Reflux; Stage #3: With hydrogenchloride; iron; ammonium chloride In methanol; water at 20 - 70℃; |
5-nitrothiophene-2-carbonyl chloride
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dichloromethane / 0 - 20 °C 2: 20 % Pd(OH)2/C; hydrogen / ethanol View Scheme |
methyl 5-aminothiophene-2-carboxylate
1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
C13H13N3O4S
Conditions | Yield |
---|---|
With acetic acid for 6h; Reflux; | 94% |
methyl 5-aminothiophene-2-carboxylate
C17H25N5O3SSi
C22H28N6O3SSi
Conditions | Yield |
---|---|
Stage #1: methyl 5-aminothiophene-2-carboxylate; C17H25N5O3SSi With sodium hydride In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: With water; ammonium chloride In dimethyl sulfoxide | 85% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; |
methyl 5-aminothiophene-2-carboxylate
ethyl 4,4,4-trifluoroacetoacetate
2-carbomethoxy-4-trifluoromethylthieno[2,3-b]pyridin-6-one
Conditions | Yield |
---|---|
In acetic acid Heating; | 84% |
methyl 5-aminothiophene-2-carboxylate
1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione
Conditions | Yield |
---|---|
In acetic acid Heating; | 78% |
methyl 5-aminothiophene-2-carboxylate
N-(1-chloro-2,2,2-trifluoroethylidene)-O-methylurethane
Conditions | Yield |
---|---|
With triethylamine In benzene at 20℃; for 2h; | 78% |
methyl 5-aminothiophene-2-carboxylate
3,3-dimethoxy-2-formyl-propanenitrile sodium salt
Conditions | Yield |
---|---|
Stage #1: methyl 5-aminothiophene-2-carboxylate; 3,3-dimethyloxy-2-formylpropionitrile sodium salt With hydrogenchloride In methanol; water at 20℃; for 4h; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 12h; | 78% |
methyl 5-aminothiophene-2-carboxylate
methyl 5-(3-(difluoromethoxy)-2-nitrophenylamino)thiophene-2-carboxylate
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80 - 90℃; for 0.25h; Inert atmosphere; | 77.5% |
methyl 5-aminothiophene-2-carboxylate
3-fluoro-2-nitrobenzonitrile
methyl 5-(3-cyano-2-nitrophenylamino)thiophene-2-carboxylate
Conditions | Yield |
---|---|
With triethylbutylammonium chloride; potassium hydroxide In N,N-dimethyl-formamide Cooling with ice; | 77% |
methyl 5-aminothiophene-2-carboxylate
1-Phenyl-4,4,4-trifluorobutane-1,3-dione
Conditions | Yield |
---|---|
In acetic acid Heating; | 73% |
methyl 5-aminothiophene-2-carboxylate
methyl N-(1,2,2,2-tetrachloroethylidene)urethan
Conditions | Yield |
---|---|
With triethylamine In benzene at 20℃; for 2h; | 73% |
methyl 5-aminothiophene-2-carboxylate
di-tert-butyl dicarbonate
methyl 5-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate
Conditions | Yield |
---|---|
In tetrahydrofuran for 48h; Reflux; | 68% |
In tetrahydrofuran for 72h; Heating / reflux; | |
at 110℃; for 1.5h; Inert atmosphere; |
methyl 5-aminothiophene-2-carboxylate
2-(2-tert-butylphenoxy)-3-isocyanatopyridine
Conditions | Yield |
---|---|
In toluene at 80℃; for 1.5h; Microwave irradiation; | 63% |
methyl 5-aminothiophene-2-carboxylate
N-(2-bromo-6-methylphenyl)acetamide
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; bis(2',6'-diisopropoxybiphenyl)cyclohexylphosphine In tert-butyl alcohol at 120℃; for 2h; Molecular sieve; Microwave irradiation; | 61% |
methyl 5-aminothiophene-2-carboxylate
1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea
Conditions | Yield |
---|---|
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; | 53% |
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; |
methyl 5-aminothiophene-2-carboxylate
(N-methyl)benzimidoyl chloride
2-methoxycarbonyl-5-(α-methylaminobenzylidene)aminothiophene
Conditions | Yield |
---|---|
With triethylamine In benzene at 25℃; for 12h; | 47% |
methyl 5-aminothiophene-2-carboxylate
2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate
Conditions | Yield |
---|---|
With sodium methylate In methanol for 12h; Reflux; | 43% |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 100℃; Inert atmosphere; | 41% |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: 1-[(tert-butoxy)carbonyl]-4-[(dimethylamino)methyl]piperidine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl 5-aminothiophene-2-carboxylate In N,N-dimethyl-formamide at 30℃; for 18h; | 39% |
2-amino-4,5,6,7,8,9-hexahydro-cycloocta[b]thiophene-3-carboxylic acid isopropyl ester
methyl 5-aminothiophene-2-carboxylate
bis(trichloromethyl) carbonate
Conditions | Yield |
---|---|
Stage #1: 2-amino-4,5,6,7,8,9-hexahydro-cycloocta[b]thiophene-3-carboxylic acid isopropyl ester; bis(trichloromethyl) carbonate With triethylamine In dichloromethane at 20℃; for 2h; Stage #2: methyl 5-aminothiophene-2-carboxylate In dichloromethane at 20℃; for 1h; | 27% |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; | 8.7% |
methyl 5-aminothiophene-2-carboxylate
methyl 5-aminothiophene-2-carboxylate
benzyl isothiocyanate
5-(3-benzyl-ureido)-thiophene-2-carboxylic acid methyl ester
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 73 percent / Et3N / benzene / 2 h / 20 °C 2: 79 percent / toluene / 3 h / 110 °C View Scheme |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / Et3N / benzene / 2 h / 20 °C 2: 76 percent / toluene / 3 h / 110 °C View Scheme |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / acetic acid / Heating 2: POCl3 / 3 h / Heating View Scheme |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / acetic acid / Heating 2: POCl3 / 3 h / Heating 3: Et3N / benzene / 1.5 h / 20 °C View Scheme |
methyl 5-aminothiophene-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / acetic acid / Heating 2: 73 percent / Et3N / dioxane / 16 h / Heating 3: 75 percent / i-Pr2NEt / dioxane / Heating View Scheme |
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