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inquiryAs a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch
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inquiryCAS: 3189-13-7 MF: C9H9NO MW: 147.17 EINECS: 221-689-6 Mol File: 3189-13-7.mol Appearance:White powder
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6-Methoxyindole-2-carboxylic acid
6-methoxylindole
Conditions | Yield |
---|---|
In quinoline for 0.2h; microwave; | 99% |
With copper In quinoline for 2h; Heating; | 97.6% |
With quinoline; copper Heating; | 87% |
With quinoline; copper at 220℃; for 0.2h; Microwave irradiation; | 70% |
With quinoline; copper oxide-chromium oxide at 200 - 210℃; |
tert-butyl 6-methoxy-1H-indole-1-carboxylate
6-methoxylindole
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 1h; Heating; | 98% |
6-methoxy-N-(toluenesulfonyl)indole
6-methoxylindole
Conditions | Yield |
---|---|
With magnesium In methanol at 20℃; for 1.5h; Sonication; | 96% |
1-(E)-(2-(4-methoxy-2-nitrophenyl)vinyl)pyrrolidine
6-methoxylindole
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In ethanol at 75℃; for 7h; | 93% |
(5-bromo-4-methoxy-2-nitrophenyl)acetonitrile
6-methoxylindole
Conditions | Yield |
---|---|
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature; | 90% |
6-methoxylindole
Conditions | Yield |
---|---|
Stage #1: 6-methoxy-1-tosylindoline In tetrahydrofuran at -78℃; for 2h; Stage #2: With oxygen In tetrahydrofuran at 20℃; | 86% |
acetaldehyde 3-methoxyphenylhydrazone
A
6-methoxylindole
B
4-methoxy-1H-indole
Conditions | Yield |
---|---|
GIPKh-115 In benzene at 260 - 280℃; (g) phase; | A n/a B 85% |
GIPKh-115 In benzene at 180 - 320℃; (g) phase. Object of study: effect of electronic factors; | A n/a B 85% |
GIPKh-115 at 260 - 280℃; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Stage #1: 6-methoxy-2,3-dihydro-1H-indole In tetrahydrofuran at -78℃; for 2h; Stage #2: With oxygen In tetrahydrofuran at 20℃; | 85% |
With potassium tert-butylate In o-xylene at 140℃; for 36h; Inert atmosphere; | 70% |
With oxygen In N,N-dimethyl acetamide at 20℃; Schlenk technique; Irradiation; | 44% |
With monoamine oxidase D11 In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 168h; pH=7.8; Enzymatic reaction; | 40% |
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane 2.1: / tetrahydrofuran / 2 h / -78 °C 2.2: 20 °C View Scheme |
6-methoxylindole
Conditions | Yield |
---|---|
With hydrogenchloride; iron; acetic acid In ethanol Temp. 70 - 75 deg C, 1 h. Temp. 85 deg C, 2 h; | 84% |
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide for 12h; | 73% |
A
6-methoxylindole
B
6-methoxy-2,3-dihydro-1H-indole
C
2-(2-amino-ethyl)-5-methoxy-phenylamine
Conditions | Yield |
---|---|
With hydrogen; acetic acid; palladium on activated charcoal In ethanol; water at 25℃; under 2585.74 Torr; for 18h; | A 73% B n/a C n/a |
1-(2-Bromo-2-chloro-ethyl)-4-methoxy-2-nitro-benzene
6-methoxylindole
Conditions | Yield |
---|---|
With sodium acetate; iron; acetic acid In ethanol; water for 2h; Heating; | 71% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at -20℃; for 0.166667h; | 68% |
6-methoxylindole
Conditions | Yield |
---|---|
With quinoline; copper at 220℃; for 0.2h; Microwave irradiation; | 56% |
Multi-step reaction with 2 steps 1: tetrakis(trifluoroacetato)rhodium(II) / toluene / 0.25 h / 100 °C / Microwave irradiation 2: quinoline; copper / 0.2 h / 220 °C / Microwave irradiation View Scheme |
ethene
4-bromo-3-nitroanizole
A
6-methoxylindole
B
1-methoxy-3-nitro-4-vinylbenzene
Conditions | Yield |
---|---|
With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate In acetonitrile at 120℃; under 22800 Torr; for 24h; | A 48% B 32% |
Conditions | Yield |
---|---|
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile at 100℃; for 20h; sealed tube; | 46% |
4-methoxy-1-ethyl-2-nitrobenzene
6-methoxylindole
Conditions | Yield |
---|---|
With tetrakis(trifluoroacetato)rhodium(II); caesium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Schlenk technique; Inert atmosphere; | 45% |
1-methoxy-3-nitro-4-vinylbenzene
6-methoxylindole
Conditions | Yield |
---|---|
With carbon monoxide; triphenylphosphine; palladium diacetate In acetonitrile under 3040 Torr; for 21h; Heating; | 40% |
Multi-step reaction with 2 steps 1: 65 percent / O2 (1 atm) / Na2PdCl4 / 24 h 2: 84 percent / Fe, acetic acid, 10percent HCl / ethanol / Temp. 70 - 75 deg C, 1 h. Temp. 85 deg C, 2 h View Scheme | |
Multi-step reaction with 2 steps 1: 80 percent / oxygen / palladium(II) chloride, copper(I) chloride / 1,2-dimethoxy-ethane / 24 h / 50 - 60 °C 2: 1.) H2, 2.) aq. HCl / 10percent rhodium-carbon / 1.) ethanol, room temperature, 1 atmosphere, 3 h, 2.) room temperature, 3 h View Scheme |
N-(3-methoxyphenyl)ethenesulfinamide
A
6-methoxylindole
B
4-methoxy-1H-indole
Conditions | Yield |
---|---|
In toluene at 110℃; for 1h; | A 25% B 5% |
2,β-Dinitro-4-methoxy-styrol
6-methoxylindole
Conditions | Yield |
---|---|
With palladium on activated charcoal; ethanol; ethyl acetate Hydrogenation.Reagens 4: Essigsaeure; | |
With ethanol; iron; acetic acid |
pyrrolidine
4-Methyl-3-nitroanisole
N,N-dimethyl-formamide dimethyl acetal
6-methoxylindole
Conditions | Yield |
---|---|
With ammonium acetate; titanium(III) chloride 1) DMF, 100-110 deg C, 3 h, 2) water, DMF, 15 min; Yield given. Multistep reaction; |
4-Methyl-3-nitroanisole
6-methoxylindole
Conditions | Yield |
---|---|
With pyrrolidine; dimethylamide dimethyl acetal; hydrogen; palladium on activated charcoal 1.) DMF, 105 deg C, 19 h, 2.) ethyl acetate, 50 p.s.i., 3 h; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: 4 h / 110 °C 2: TiCl3, 4M NH4OAc / acetone View Scheme | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 h / 115 °C / Inert atmosphere 2: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 7 h / 75 °C View Scheme |
2-(4-methoxy-2-nitrophenyl)acetaldehyde
6-methoxylindole
Conditions | Yield |
---|---|
With sodium acetate; iron; acetic acid In ethanol; water for 2h; Heating; Yield given; |
6-methoxylindole
Conditions | Yield |
---|---|
With titanium(III) chloride; ammonium acetate In acetone Yield given; |
Acetic acid 1-chloro-2-(4-methoxy-2-nitro-phenyl)-ethyl ester
6-methoxylindole
Conditions | Yield |
---|---|
With sodium acetate; iron; acetic acid In ethanol; water for 2h; Heating; |
N-(2,2-Diethoxy-ethyl)-2,2,2-trifluoro-N-(3-methoxy-phenyl)-acetamide
A
6-methoxylindole
B
4-methoxy-1H-indole
Conditions | Yield |
---|---|
With potassium hydroxide; trifluoroacetic anhydride 1) CF3COOH, 56 deg C, 56 h; 2) methanol, room temperature; Yield given. Multistep reaction. Yields of byproduct given; |
2-<(4-methoxy-2-nitrophenyl)methyl>-1,3-dioxane
6-methoxylindole
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; rhodium contaminated with carbon 1.) ethanol, room temperature, 1 atmosphere, 3 h, 2.) room temperature, 3 h; Yield given. Multistep reaction; |
triethanolamine
m-Anisidine
A
6-methoxylindole
B
4-methoxy-1H-indole
Conditions | Yield |
---|---|
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane at 180℃; for 20h; Yield given. Yields of byproduct given; |
6-methoxylindole
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0℃; for 0.5h; | 100% |
Stage #1: 6-methoxylindole With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide | 100% |
With sodium cyanoborohydride; acetic acid at 20℃; for 3h; | 97% |
6-methoxylindole
N,N-dimethyl(methylene)ammonium chloride
1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine
Conditions | Yield |
---|---|
In dichloromethane | 100% |
6-methoxylindole
p-methoxybenzyl chloride
6-methoxy-N-(4-methoxybenzyl)indole
Conditions | Yield |
---|---|
Stage #1: 6-methoxylindole With sodium hydride In N,N-dimethyl-formamide at 25℃; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 25℃; for 12h; | 100% |
6-methoxylindole
(C-benzyloxymethane-N-benzyl)nitrone
1-[N-benzyl-N-(hydroxy)amino]-2-[N'-(tert-butoxycarbonyl)amino]-1-(6'-methoxyindol-3'-yl)ethane
Conditions | Yield |
---|---|
Stage #1: 6-methoxylindole; (C-benzyloxymethane-N-benzyl)nitrone With hydrogenchloride In methanol at 0℃; Stage #2: With sodium hydrogencarbonate In methanol; water | 100% |
6-methoxylindole
benzenesulfonyl chloride
6-methoxy-1-(phenylsulfonyl)-1H-indole
Conditions | Yield |
---|---|
Stage #1: 6-methoxylindole With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 4℃; Inert atmosphere; Sealed tube; Stage #2: benzenesulfonyl chloride In dichloromethane at 4 - 23℃; for 3h; Inert atmosphere; Sealed tube; | 99% |
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; | 93.8% |
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃; for 1h; | 92% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; | 99% |
With potassium hydroxide In dimethyl sulfoxide at 20℃; | 93% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; | 91% |
maleiimide
6-methoxylindole
3-(6-methoxy-1H-indol-3-yl)pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
With acetic acid at 190℃; for 2h; Michael addition; microwave irradiation; | 99% |
In acetic acid at 170℃; for 2h; Microwave irradiation; |
6-methoxylindole
methyl 4-phenyl-2-oxo-3-butenoate
Conditions | Yield |
---|---|
With C35H48N4O4; samarium(III) trifluoromethanesulfonate In dichloromethane at -20℃; for 0.5h; asymmetric Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; | 99% |
6-methoxylindole
tert-butyl 3-((tert-butoxycarbonyl)imino)-2-oxoindoline-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: tert-butyl 3-((tert-butoxycarbonyl)imino)-2-oxoindoline-1-carboxylate With C33H48N4O4; zinc trifluoromethanesulfonate In toluene at 35℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: 6-methoxylindole In toluene at 50℃; for 48h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; enantioselective reaction; | 99% |
6-methoxylindole
Conditions | Yield |
---|---|
Stage #1: C16H18N2O5 With C33H48N4O4; zinc trifluoromethanesulfonate In toluene at 35℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: 6-methoxylindole In toluene at 50℃; for 48h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; enantioselective reaction; | 99% |
6-methoxylindole
Conditions | Yield |
---|---|
Stage #1: 3-(1-phenylvinyl)-1H-indole With C76H57F12NO6P2 In 1,2-dichloro-ethane at -20℃; for 0.166667h; Molecular sieve; Stage #2: 6-methoxylindole In 1,2-dichloro-ethane at -20℃; for 24h; Molecular sieve; enantioselective reaction; | 99% |
6-methoxylindole
N,N-dimethyl-formamide
6-methoxy-1H-indole-3-carbaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate at 20℃; for 2.5h; | 98% |
With trichlorophosphate at 0 - 40℃; Vilsmeier formylation; | 89% |
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.333333h; Vilsmeier-Haack Formylation; Cooling with ice; Stage #2: 6-methoxylindole at 20℃; for 1.5h; Vilsmeier-Haack Formylation; | 59% |
6-methoxylindole
tert-butyldimethylsilyl chloride
1-(tert-butyldimethylsilyl)-6-methoxy-1H-indole
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 10h; | 98% |
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 6h; Inert atmosphere; | 79% |
Stage #1: 6-methoxylindole With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.25h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 0℃; for 3h; |
6-methoxylindole
(2-bromo-ethoxy)-tert-butyl-dimethyl-silane
1-[2-(tert-butyldimethylsilyloxy)-eth-1-yl]-6-methoxy-1H-indole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | 98% |
6-methoxylindole
ethyl 5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate
ethyl (R)-3-(6-methoxy-1H-indol-3-yl)-5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate
Conditions | Yield |
---|---|
With C38H33O4P In toluene at -78℃; for 6h; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With C18H18Cl4N2Ni2O2; potassium 2-methylbutan-2-olate In neat (no solvent) at 140℃; for 6h; | 98% |
Stage #1: 6-methoxylindole; benzyl alcohol With potassium phosphate; C24H20FeN2O4 In neat (no solvent) at 20℃; for 2h; Schlenk technique; Inert atmosphere; UV-irradiation; Stage #2: In neat (no solvent) at 110℃; for 16h; Schlenk technique; Inert atmosphere; | 73% |
6-methoxylindole
ethyl-4-cyanobenzoylformate
Conditions | Yield |
---|---|
With PHN-DHQ-OH In diethyl ether at 23℃; for 58h; Friedel-Crafts reaction; | 97% |
6-methoxylindole
ethyl-4-cyanobenzoylformate
Conditions | Yield |
---|---|
With 4-((S)-(phenanthren-9-yloxy)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methyl)quinolin-6-ol In diethyl ether at 23℃; for 59h; Friedel-Crafts reaction; | 97% |
6-methoxylindole
2-nitrobenzenesulfenyl chloride
6-methoxy-3-(2-nitro-phenylsulfanyl)-1H-indole
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 1.06667h; | 97% |
6-methoxylindole
triisopropylsilyl chloride
Conditions | Yield |
---|---|
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; | 97% |
6-methoxylindole
formaldehyd
dimethyl amine
1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine
Conditions | Yield |
---|---|
In acetic acid for 15h; Ambient temperature; | 96% |
With ethanol; acetic acid | |
With 1,4-dioxane; acetic acid | |
With acetic acid at 0 - 20℃; for 4h; | |
With acetic acid at 0 - 25℃; for 12h; |
6-methoxylindole
di-tert-butyl dicarbonate
tert-butyl 6-methoxy-1H-indole-1-carboxylate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 8h; Inert atmosphere; | 96% |
With dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | 90% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; | 89% |
With dmap In dichloromethane at 40℃; | 86% |
6-methoxylindole
acetyl chloride
1-(6-methoxy-1H-indol-3-yl)ethan-1-one
Conditions | Yield |
---|---|
Stage #1: 6-methoxylindole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Stage #2: acetyl chloride In hexane; dichloromethane at 50℃; for 0.166667h; microwave irradiation; Further stages.; | 96% |
Stage #1: 6-methoxylindole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride In hexane; dichloromethane at 0℃; Inert atmosphere; | |
Stage #1: 6-methoxylindole; acetyl chloride In toluene at 0℃; for 0.166667h; Stage #2: With tin(IV) chloride In toluene for 12h; | |
Stage #1: 6-methoxylindole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride In hexane; dichloromethane at 0℃; Inert atmosphere; |
p-nitrobenzene iodide
6-methoxylindole
6-methoxy-1-(4-nitrophenyl)-1H-indole
Conditions | Yield |
---|---|
With 1,2-ethanedione dioxime; tetrabutylammomium bromide; copper(l) chloride; sodium hydroxide In water at 100℃; for 24h; Inert atmosphere; sealed tube; | 96% |
6-methoxylindole
cyanoacetic acid
3-(6-methoxy-1H-indol-3-yl)-3-oxopropanenitrile
Conditions | Yield |
---|---|
With propionic acid anhydride at 65 - 75℃; for 0.116667h; | 96% |
With propionic acid anhydride at 100℃; |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 20℃; | 96% |
6-methoxylindole
1-phenylmethyl-4-piperidone
6-methoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
Conditions | Yield |
---|---|
With sodium methylate In methanol for 5h; Heating; | 95% |
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