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N-{2-[5-(benzyloxy)-1H-indol-3-yl]ethyl}acetamide
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With hydrogen; nickel In ethanol under 2068.6 Torr; | 95% |
With palladium 10% on activated carbon; hydrogen; ammonium formate In ethanol for 2h; Reflux; Inert atmosphere; | 85% |
With hydrogen; nickel | |
With palladium on activated charcoal; hydrogen In ethyl acetate |
vinyl acetate
3-(2-aminoethyl)-1H-indol-5-ol
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction; chemoselective reaction; | 85% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 50℃; under 3000.3 Torr; for 12h; Inert atmosphere; | 71% |
3-(2-acetamidoethyl)-1H-indol-5-yl acetate
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 1.6h; | 65% |
With potassium carbonate In methanol at 26℃; for 2h; |
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -78 - 20℃; | 45% |
Stage #1: 5-methoxy-N-acetyl-tryptamine With boron tribromide In dichloromethane at -78℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water at -78 - 20℃; | 45% |
Nb-acetyl-1-hydroxytriptamine
A
N-acetyl-5-hydroxytryptamine
B
N,N'-diacetyl-2,2'-biindolyl-3,3'-bis(2-aminoethane)
Conditions | Yield |
---|---|
With trifluoroacetic acid | A 13% B 17% C 33% |
formic acid
Nb-acetyl-1-hydroxytriptamine
A
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
for 19h; Ambient temperature; | A 17% B 19% |
3-(2-aminoethyl)-1H-indol-5-ol
acetyl chloride
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Acetylation; |
Conditions | Yield |
---|---|
With sheep pineal supernatant (serotonin-N-acetyl transferase); Pargyline In phosphate buffer at 37℃; for 0.166667h; pH=6.8; Enzyme kinetics; |
5-benzyloxytryptamine
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / aq. HCl, NaOAc / 1 h 2: 95 percent / H2 / Raney nickel / ethanol / 2068.6 Torr View Scheme | |
Multi-step reaction with 2 steps 1: NaOAc 2: H2 / Raney Ni View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme |
Conditions | Yield |
---|---|
With sodium acetate; acetic anhydride In hydrogenchloride; methanol; ethanol |
Conditions | Yield |
---|---|
With sodium hydroxide; acetic anhydride |
3-(2-aminoethyl)-1H-indol-5-ol
acetylcoenzyme A
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With sea bream arylalkylamine N-acetyltransferase containing I157M mutation at β5 region Kinetics; Reagent/catalyst; Enzymatic reaction; | |
With 5,5'-dithiobis-(2-nitrobenzoic acid); Drosophila melanogaster arylalkylamine N-acetyltransferase A from E. coli In aq. buffer pH=8; Kinetics; Enzymatic reaction; | |
With dipyridin-4-yl disulfide; wild-type arylalkylamine N-acyltransferase from Tribolium castaneum In aq. buffer pH=8; Kinetics; Enzymatic reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 20 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen; ammonium formate / ethanol / 2 h / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 0 °C 2: triethylamine / dichloromethane 3: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 5 h / 0 - 26 °C 2: potassium carbonate / methanol / 2 h / 26 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate / methanol / 1.6 h / 20 °C View Scheme |
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With Helix pomatia arylsulfatase In aq. acetate buffer at 21℃; for 24h; Catalytic behavior; Enzymatic reaction; | |
With arylsulfatase from Helix pomatia In aq. acetate buffer at 21℃; for 24h; pH=7; Enzymatic reaction; |
3-(2-aminoethyl)-1H-indol-5-ol
ethyl acetate
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction; chemoselective reaction; |
Conditions | Yield |
---|---|
With acetylcoenzyme A In aq. phosphate buffer at 45℃; for 1h; pH=7.8; Enzymatic reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: acetic acid 2: N,N-dimethyl-formamide; water / 80 °C 3: lithium aluminium tetrahydride / diethyl ether / 0 °C 4: triethylamine / dichloromethane 5: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; water / 80 °C 2: lithium aluminium tetrahydride / diethyl ether / 0 °C 3: triethylamine / dichloromethane 4: palladium on activated charcoal; hydrogen / ethyl acetate View Scheme |
N-acetyl-5-hydroxytryptamine
Nb-acetyltryptamine-4,5-dione
Conditions | Yield |
---|---|
With potassium nitrososulfonate In methanol; water at 0℃; for 0.5h; | 99% |
With potassiuim nitrosodisulfonate In water for 3h; | 11 mg |
(E)-3-(2-(trifluoromethyl)phenyl)acrylic acid
N-acetyl-5-hydroxytryptamine
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 3.5h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h; Inert atmosphere; | 96% |
diazomethane
N-acetyl-5-hydroxytryptamine
Nb-acetyl-1-methoxytryptamine
Conditions | Yield |
---|---|
In methanol Ambient temperature; | 94% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2.5h; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 3h; Inert atmosphere; | 71% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 68% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile Reflux; Inert atmosphere; | 63% |
N-acetyl-5-hydroxytryptamine
dimethyl sulfate
5-methoxy-N-acetyl-tryptamine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 26℃; for 2.25h; | 61.4% |
N-acetyl-5-hydroxytryptamine
4-Nitrophenyl chloroformate
3-[2-(acetylamino)ethyl]-1H-indol-5-yl 4-nitrophenyl carbonate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In tetrahydrofuran for 0.5h; Inert atmosphere; | 60% |
With 4-methyl-morpholine |
N-acetyl-5-hydroxytryptamine
tert-butyl 6-bromohexylcarbamate
Conditions | Yield |
---|---|
Stage #1: N-acetyl-5-hydroxytryptamine With potassium carbonate In acetonitrile for 1h; Reflux; Inert atmosphere; Stage #2: tert-butyl 6-bromohexylcarbamate With sodium iodide In acetonitrile for 20h; Reflux; Inert atmosphere; | 59% |
N-acetyl-5-hydroxytryptamine
ethyl isocyanate
carbamic acid 3-(2-acetylamino-ethyl)-1H-indol-5-yl ethyl ester
Conditions | Yield |
---|---|
With sodium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 57% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 57% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere; | 56% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 55% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 55% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 53% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere; | 50% |
N-acetyl-5-hydroxytryptamine
2-bromomethylnaphthyl bromide
N-{2-[5-(naphthalen-2-ylmethoxy)-1H-indol-3-yl]ethyl}-acetamide
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere; | 47% |
N-acetyl-5-hydroxytryptamine
8-amino>octyl bromide
Conditions | Yield |
---|---|
Stage #1: N-acetyl-5-hydroxytryptamine With potassium carbonate In acetonitrile for 1h; Reflux; Inert atmosphere; Stage #2: 8-amino>octyl bromide With sodium iodide In acetonitrile for 20h; Reflux; Inert atmosphere; | 47% |
Conditions | Yield |
---|---|
Stage #1: N-acetyl-5-hydroxytryptamine With sodium hydride In ethanol for 0.5h; Stage #2: 1,3-dibromo-propane In ethanol at 60℃; for 3h; Inert atmosphere; | 46% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 60℃; for 4h; Reflux; Inert atmosphere; | 43% |
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