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N-triisopropylsilylpyrrole
N,N-dimethyl-formamide
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With phosgene In dichloromethane at 0℃; for 0.5h; Stage #2: N-triisopropylsilylpyrrole In dichloromethane for 0.5h; Reflux; Stage #3: With sodium hydroxide at 20℃; for 12h; | 98% |
Stage #1: N,N-dimethyl-formamide With oxalyl dichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: N-triisopropylsilylpyrrole In dichloromethane at 50℃; for 0.5h; Inert atmosphere; Stage #3: With sodium hydroxide at 20℃; Inert atmosphere; | 85% |
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1.5h; Vilsmeier-Haack Formylation; Stage #2: N-triisopropylsilylpyrrole In dichloromethane for 2h; | 71.9% |
1-(triisopropylsilyl)-1H-pyrrole-3-carbaldehyde
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride | 86% |
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.0833333h; Ambient temperature; | 86% |
With sodium hydroxide for 4h; Inert atmosphere; |
4-formyl-1H-pyrrole-2-carboxylic acid
A
pyrrole-3-carboxaldehyde
B
carbon dioxide
Conditions | Yield |
---|---|
With copper chromite In quinoline at 185℃; for 0.2h; | A 76% B n/a |
N-triisopropylsilylpyrrole
Vilsmeier reagent
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide | 72% |
2,4,5-triiodo-3-formylpyrrole
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With hydrogen; sodium acetate; palladium on activated charcoal In ethanol under 2585.7 Torr; for 2h; | 70% |
isopropylidene-(1H-pyrrol-3-yl)-ammonium chloride
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide for 4h; Ambient temperature; | 69% |
With sodium hydroxide In water at 20℃; for 2h; | 37.6% |
With sodium hydroxide; water at 20℃; for 4h; |
(E)-1,1-difluoro-4-ethoxy-2-(aminomethyl)-3-buten-2-ol
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetonitrile at 20℃; for 24h; | 48% |
Vilsmeier reagent
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: pyrrole With sodium hydride In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With triisopropylsilyl chloride In tetrahydrofuran at 0 - 10℃; for 1.5h; Stage #3: Vilsmeier reagent With sodium hydroxide; water more than 3 stages; | 38% |
Vilsmeier reagent
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 1-(trisopropylsilyl)pyrrole; Vilsmeier reagent In dichloromethane at 0℃; Vilsmeier formylation; Reflux; Stage #2: With water; sodium hydroxide at 20℃; for 2h; | 38% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid | 22% |
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane for 21h; Heating; | 3 g |
N-(hydroxy-2' ethyl)amino-3 propenoate d'ethyle
A
pyrrole carboxaldehyde
B
2-pyrrole aldehyde
C
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
In tetrahydrofuran at 400℃; sealed tube; | A n/a B 16% C 19% |
In tetrahydrofuran at 400℃; sealed tube; | A n/a B n/a C 19% |
3-<(2-tosylhydrazino)carbonyl>pyrrole
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium carbonate In ethylene glycol at 170℃; for 0.0833333h; | 15% |
(+)-D-glucosamine hydrochloride
A
pyrrole-3-carboxaldehyde
B
5-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde
C
5-(β-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
D
5-(α-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
(+)-D-glucosamine hydrochloride
A
pyrrole-3-carboxaldehyde
B
5-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde
C
5-(α-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
Conditions | Yield |
---|---|
With sodium carbonate 1) H2O, room temp., 24h, 2) 90 deg C, 1h; Yield given. Multistep reaction. Yields of byproduct given; |
2-deoxy-2-<(3'-oxo-1'-propen-1'-yl)amino>-α-D-glucopyranose
A
pyrrole-3-carboxaldehyde
B
5-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde
C
5-(β-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
D
5-(α-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
Conditions | Yield |
---|---|
With sodium carbonate In water-d2 at 90℃; for 1h; Yield given. Yields of byproduct given; |
N-triisopropylsilylpyrrole
N,N-dimethyl-formamide
A
2-pyrrole aldehyde
B
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide; pyrophosphoryl chloride 1) acetonitrile, 20 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
N-triisopropylsilylpyrrole
N-methyl-N-phenylformamide
A
2-pyrrole aldehyde
B
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide; pyrophosphoryl chloride 1) acetonitrile, 20 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; | |
Yield given. Multistep reaction. Yields of byproduct given; |
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In acetonitrile at 20℃; for 0.5h; |
1-diethoxymethyl-1H-pyrrole-3-carbaldehyde
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / acetonitrile / 1 h / 20 °C 2: aq. NaOH / acetonitrile / 0.5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrazine / 2 h / Heating 2: pyridine / 0.5 h / 20 °C 3: 15 percent / sodium carbonate / ethane-1,2-diol / 0.08 h / 170 °C View Scheme |
pyrrole-3-carboxylic acid hydrazide
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 0.5 h / 20 °C 2: 15 percent / sodium carbonate / ethane-1,2-diol / 0.08 h / 170 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 1 h / 0 - 130 °C / Inert atmosphere; Microwave irradiation 2: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere 3: manganese(IV) oxide / methanol / 20 °C View Scheme |
pyrrole-3-carboxylic acid ethyl ester
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere 2: manganese(IV) oxide / methanol / 20 °C View Scheme |
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With manganese(IV) oxide In methanol at 20℃; |
Conditions | Yield |
---|---|
Stage #1: pyrrole With sodium hydride In tetrahydrofuran at -10℃; for 1.5h; Stage #2: With triisopropylsilyl chloride In tetrahydrofuran at 20℃; Stage #3: N,N-dimethyl-formamide With oxalyl dichloride In dichloromethane at -10℃; for 4h; |
pyrrole-3-carboxaldehyde
dichloromethane
1,1'-methylenebis(1H-pyrrole-2-carboxaldehyde)
Conditions | Yield |
---|---|
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane for 5h; | 98% |
Conditions | Yield |
---|---|
With caesium carbonate; sodium iodide In acetonitrile at 80℃; for 16h; Sealed tube; | 98% |
Conditions | Yield |
---|---|
Stage #1: Hippuric Acid With triethylamine sulfate at 80℃; for 0.0833333h; Green chemistry; Stage #2: pyrrole-3-carboxaldehyde at 100℃; for 0.333333h; Reagent/catalyst; Green chemistry; stereoselective reaction; | 97% |
Stage #1: Hippuric Acid; pyrrole-3-carboxaldehyde With sodium acetate; acetic anhydride for 2h; Heating; Stage #2: In ethanol at 20℃; for 18h; Stage #3: With PPA at 80 - 90℃; for 2h; | 60% |
Conditions | Yield |
---|---|
In acetonitrile Ambient temperature; | 95% |
pyrrole-3-carboxaldehyde
4,4,4‐trifluoro‐1‐phenyl‐2‐buten‐1‐one
Conditions | Yield |
---|---|
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In toluene at 40℃; for 24h; | 95% |
pyrrole-3-carboxaldehyde
pyrrole-3-carboxaldehyde oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; potassium carbonate In water for 0.5h; Heating; | 94% |
pyrrole-3-carboxaldehyde
di-tert-butyl dicarbonate
tert-butyl 3-formylpyrrole-1-carboxylate
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane 0 deg C, 3 h then r.t., 1 h; | 93% |
In acetonitrile at 25℃; for 24h; |
pyrrole-3-carboxaldehyde
orthoformic acid triethyl ester
1-diethoxymethyl-1H-pyrrole-3-carbaldehyde
Conditions | Yield |
---|---|
for 24h; Heating; | 92% |
Conditions | Yield |
---|---|
In acetonitrile Ambient temperature; | 91% |
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In toluene at 40℃; for 24h; | 91% |
pyrrole-3-carboxaldehyde
benzenesulfonyl chloride
1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 15℃; for 24h; | 90.95% |
2-(3-methylbutoxy)-1,3-benzodithiole
pyrrole-3-carboxaldehyde
2,5-bis(1,3-benzodithiol-2-yl)-3-formylpyrrole
Conditions | Yield |
---|---|
With acetic acid at 70℃; for 2h; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere; | 90% |
In tetrahydrofuran |
pyrrole-3-carboxaldehyde
Conditions | Yield |
---|---|
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In toluene at 40℃; for 24h; | 90% |
pyrrole-3-carboxaldehyde
Malonic acid monomethyl ester
(Z)-3-(1H-Pyrrol-3-yl)-acrylic acid methyl ester
Conditions | Yield |
---|---|
With piperidine In pyridine at 65℃; for 21h; | 89% |
Conditions | Yield |
---|---|
In ethanol at 80℃; Wittig Olefination; | 89% |
pyrrole-3-carboxaldehyde
p-toluenesulfonyl chloride
3-formyl-1-<(4-methylphenyl)sulfonyl>pyrrole
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 0.25h; cooled; | 88% |
Stage #1: pyrrole-3-carboxaldehyde With sodium hydroxide In dichloromethane at 0℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 0 - 20℃; for 19h; | 88% |
Stage #1: pyrrole-3-carboxaldehyde With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 4h; Inert atmosphere; | 77% |
With dmap; triethylamine In dichloromethane at 20℃; for 12h; | |
With triethylamine In dichloromethane at 20℃; |
pyrrole-3-carboxaldehyde
benzyl bromide
1-benzyl-1H-pyrrole-3-carbaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 0 - 20℃; | 88% |
Conditions | Yield |
---|---|
In acetonitrile at 60℃; Mannich Aminomethylation; | 87% |
Conditions | Yield |
---|---|
Stage #1: C14H23O8PS With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Wittig-Horner Reaction; Inert atmosphere; Stage #2: pyrrole-3-carboxaldehyde In tetrahydrofuran for 1h; Wittig-Horner Reaction; Inert atmosphere; | 86.7% |
pyrrole-3-carboxaldehyde
diphenyl hydrogen phosphite
4,4'-diamino diphenyl methane
Conditions | Yield |
---|---|
at 80℃; for 4h; Kabachnik-Fields Reaction; Green chemistry; | 86% |
Conditions | Yield |
---|---|
With 16-crown-6; potassium tert-butylate In cyclohexane; dimethyl sulfoxide | 85% |
Stage #1: pyrrole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; | 35% |
Stage #1: pyrrole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1h; | 35% |
With sodium hydride In tetrahydrofuran for 4.25h; Inert atmosphere; | 610 mg |
Conditions | Yield |
---|---|
Stage #1: pyrrole-3-carboxaldehyde With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.833333h; Stage #2: allyl bromide In dimethyl sulfoxide at 20℃; for 4h; | 84% |
pyrrole-3-carboxaldehyde
acrylic acid methyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Reflux; | 84% |
Conditions | Yield |
---|---|
With piperidine In ethanol at 65℃; for 2h; | 83% |
Conditions | Yield |
---|---|
With diammonium phosphate at 80℃; for 3.5h; | 82% |
Conditions | Yield |
---|---|
With acetic acid In methanol for 2h; Reflux; | 82% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 115℃; for 1.5h; | 80.5% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene for 1h; Wittig Olefination; Reflux; | 67 g |
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