2,3-dihydro-7-methylindole
7-methyl-1H-indole
Conditions | Yield |
---|---|
With 6C44H32N6O4Ru(2+)*12Hf(2+)*8O(2-)*14HO(1-)*6C16H22ClCoN5O6(1-) In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Irradiation; | 99% |
With H8O20P8Pt2(4-)*4C34H72N(1+) In methanol Inert atmosphere; Irradiation; | 97% |
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; chloropyridinecobaloxime(III) In ethanol at 30℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; | 89% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane at 40 - 45℃; for 40h; | 93% |
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - 45℃; for 40h; Inert atmosphere; | 93% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
Stage #1: 7-methyl-1-tosylindoline In tetrahydrofuran at -78℃; for 2h; Stage #2: With oxygen In tetrahydrofuran at 20℃; | 84% |
6-methyl-2-vinylaniline
7-methyl-1H-indole
Conditions | Yield |
---|---|
With p-benzoquinone; lithium chloride; dichloro bis(acetonitrile) palladium(II) In tetrahydrofuran for 10h; Heating; | 82% |
Conditions | Yield |
---|---|
With triphenylphosphine; tin(ll) chloride; ruthenium trichloride In 1,4-dioxane; water at 180℃; for 20h; Cyclization; | 80% |
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane; water at 180℃; for 20h; | 80% |
C9H8N2O4
7-methyl-1H-indole
Conditions | Yield |
---|---|
With indium; acetic acid In benzene at 80℃; for 5h; Inert atmosphere; | 76% |
7-methyl-1-(phenylsulfonyl)-1H-indole
7-methyl-1H-indole
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; 1,2-dimethoxyethane for 24h; Heating; | 75% |
7-methyl-2-trimethylsilanyl-indole-1-carboxylic acid diethylamide
7-methyl-1H-indole
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 12h; Heating; | 75% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -45 - -40℃; Cyclization; Bartoli reaction; | 71% |
In tetrahydrofuran at -40℃; for 0.333333h; | 67% |
In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; | 34% |
1-(2-amino-3-methylphenyl)-2-chloroethan-1-one
7-methyl-1H-indole
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 1,4-dioxane; water for 2h; Heating; | 71% |
Conditions | Yield |
---|---|
With phosphorus pentachloride; zinc(II) chloride for 0.0666667h; microwave irradiation; | 71% |
1-methyl-2-nitrobenzene
vinyl magnesium bromide
A
7-methyl-1H-indole
B
acetaldehyde
C
2,2'-dimethylazobenzene
D
o-toluidine
E
N,N'-Di-o-tolyl-diazene N-oxide
Conditions | Yield |
---|---|
In tetrahydrofuran at -40℃; for 0.333333h; other nitroarenes and vinyl Grignard reagents; | A 67% B n/a C n/a D 5% E n/a |
7-methyl-1H-indole
Conditions | Yield |
---|---|
Stage #1: (E)-1-(3-methyl-2-nitrostyryl)pyrrolidine With iron(III) chloride; pyrographite In methanol for 0.166667h; Heating; Stage #2: With hydrazine hydrate In methanol for 3h; Heating; Further stages.; | 67% |
Conditions | Yield |
---|---|
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane at 180℃; for 20h; | 66% |
Conditions | Yield |
---|---|
With o-toluidine In acetonitrile | 64.3% |
A
7-methyl-1H-indole
B
2,5-dimethylquinoxaline
D
2,8-dimethylquinoxaline
Conditions | Yield |
---|---|
at 650℃; under 0.01 Torr; | A 62% B 7% C n/a D 11% |
A
7-methyl-1H-indole
B
2,7-dimethyl-1H-indole
C
2,5-dimethylquinoxaline
D
2,8-dimethylquinoxaline
Conditions | Yield |
---|---|
at 650℃; under 0.01 Torr; | A 62% B 3% C 7% D 11% |
Conditions | Yield |
---|---|
With nickel(II) iodide; 4,4'-dimethyl-2,2'-bipyridines; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; | 60% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -45 - -40℃; Cyclization; Bartoli reaction; | 58% |
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran BH3*THF or LAH; | 55% |
A
7-methyl-1H-indole
B
2,7-dimethyl-1H-indole
C
2,5-dimethylquinoxaline
D
2,8-dimethylquinoxaline
Conditions | Yield |
---|---|
at 650℃; under 0.01 Torr; | A 55% B 5% C 4% D 17% |
2,6-dimethylnitrobenzene
N,N-dimethyl-formamide dimethyl acetal
7-methyl-1H-indole
Conditions | Yield |
---|---|
Stage #1: 2,6-dimethylnitrobenzene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 22h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere; Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis; | 53% |
7-methyl-1H-indole-5-carboxylic acid
7-methyl-1H-indole
Conditions | Yield |
---|---|
With copper(I) oxide In quinoline at 230℃; for 4h; Decarboxylation; | 50% |
A
7-methyl-1H-indole
B
1-dimethylethyl (3R)-3-hydroxy-4-(7-methyl-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 70℃; | A 48% B 36% |
A
7-methyl-1H-indole
B
5-methylquinoxaline
Conditions | Yield |
---|---|
at 650℃; under 0.01 Torr; | A 32% B 40% |
at 650℃; under 0.01 Torr; Product distribution; Mechanism; also 15N labelled; |
ethylene glycol
o-toluidine
A
7-methyl-1H-indole
B
2-(2-tolylamino)ethan-1-ol
C
1,2-bis[(2-methylphenyl)amino]ethane
D
1,4-di-o-tolyl-piperazine
Conditions | Yield |
---|---|
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube; | A 20% B 28% C n/a D n/a |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With calcium hydroxide; kieselguhr; water; nickel at 30 - 40℃; under 132391 Torr; Hydrogenation; |
7-methyl-1H-indole
Conditions | Yield |
---|---|
at 225 - 240℃; Vakuum; |
2,6-dimethylphenyl isonitrile
7-methyl-1H-indole
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine Yield given. Multistep reaction; | |
Ru(H)2(1,2-bis(dimethylphosphino)ethane)2 In benzene-d6 at 140℃; for 25h; in a sealed tube; | 98 % Spectr. |
Conditions | Yield |
---|---|
Stage #1: 7-methyl-1H-indole With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.25h; Stage #2: methyl iodide In DMF (N,N-dimethyl-formamide) at 30℃; for 1h; | 100% |
With sodium hydroxide In dimethyl sulfoxide at 20℃; | 99% |
Stage #1: 7-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; | 97% |
7-methyl-1H-indole
2,3-dihydro-7-methylindole
Conditions | Yield |
---|---|
Stage #1: 7-methyl-1H-indole 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 | 99% |
With tetrahydroxydiboron; palladium on activated carbon In 2,2,2-trifluoroethanol; water at 40℃; for 24h; Schlenk technique; | 99% |
With sodium cyanoborohydride In acetic acid; ethyl acetate | 94% |
7-methyl-1H-indole
1,1,1-trifluoroacetophenone
(R)-2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)-1-phenylethanol
Conditions | Yield |
---|---|
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at 25℃; for 48h; optical yield given as %ee; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With cupreidine 9-O-(4-(perfluoro-n-octyl)benzyl) ether In 1,1,1,3,3-pentafluorobutane; toluene at 20℃; for 1h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: 7-methyl-1H-indole With C43H64N4O4; scandium tris(trifluoromethanesulfonate); ortho-chlorobenzoic acid In dichloromethane at 30℃; for 1h; Inert atmosphere; Stage #2: glyoxylic acid ethyl ester In dichloromethane at -20℃; for 12h; Friedel Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 90% |
7-methyl-1H-indole
methyl 4-phenyl-2-oxo-3-butenoate
Conditions | Yield |
---|---|
With C35H48N4O4; samarium(III) trifluoromethanesulfonate In dichloromethane at -20℃; for 27h; asymmetric Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; | 99% |
7-methyl-1H-indole
ethyl-3,3,3-trifluoropyruvate
3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 7-methyl-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h; Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction; | 99% |
With (3aR,11aR,14aS,16bS)-2,2,13,13-tetra-isopropyl-3a,11a,14a,16b-tetrahydro-bis(1,3-dioxolano[4',5':3,4]pyrrolo)[1,2-a:1',2'-a]naphtho[1,2-d:8,7-d']diimidazole; copper(II) bis(trifluoromethanesulfonate) at 0℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; stereoselective reaction; | 97.6% |
7-methyl-1H-indole
ethyl-3,3,3-trifluoropyruvate
3,3,3-trifluoro-2-hydroxy-2-(7-methyl-1H-indol-3-yl)-propionic acid ethyl ester
Conditions | Yield |
---|---|
In 1,1,1,3,3-pentafluorobutane at 20℃; for 0.5h; Inert atmosphere; | 99% |
With triethylamine In dichloromethane at 0℃; Friedel Crafts alkylation; | |
With copper(II) bis(trifluoromethanesulfonate) In chloroform at 25℃; for 16h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
With cupreine 9-O-(4-(perfluoro-n-octyl)benzyl) ether In 1,1,1,3,3-pentafluorobutane; toluene at 20℃; for 1h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
7-methyl-1H-indole
dimethyl 2-(2,2,2-trifluoroethylidene)malonate
dimethyl (R)-2-(2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)ethyl)malonate
Conditions | Yield |
---|---|
Stage #1: dimethyl 2-(2,2,2-trifluoroethylidene)malonate With copper(II) bis(trifluoromethanesulfonate); 2,2-bis[(4S)-4-isopropyloxazolin-2-yl]propane In diethyl ether at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 7-methyl-1H-indole In diethyl ether at -35℃; for 10h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
7-methyl-1H-indole
chloromethyl methyl ether
1-methoxymethyl-7-methylindole
Conditions | Yield |
---|---|
Stage #1: 7-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil for 1h; Inert atmosphere; | 99% |
7-methyl-1H-indole
diethyl benzalmalonate
(S)-ethyl 2-ethoxycarbonyl-3-[3-(7-methylindolyl)]-3-phenylpropanoate
Conditions | Yield |
---|---|
Stage #1: diethyl benzalmalonate With 1,1-bis[(S)-4-benzyloxazolin-2-yl]-2,2-diphenylethene; copper(II) bis(trifluoromethanesulfonate) In ethanol at 20℃; for 0.5h; Friedel-Crafts alkylation; Inert atmosphere; Stage #2: 7-methyl-1H-indole In ethanol at 20℃; for 24h; Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
7-methyl-1H-indole
C11H10N2O4
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; 6-bromo-2-(((((4S,5S)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazol-2-yl)methyl)((S)-1-phenylethyl)amino)methyl)-4-nitrophenol; copper(I) triflate In toluene at 20℃; for 7h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction; | 99% |
7-methyl-1H-indole
C11H10N2O3
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; 6-bromo-2-(((((4S,5S)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazol-2-yl)methyl)((S)-1-phenylethyl)amino)methyl)-4-nitrophenol; copper(I) triflate In toluene at 20℃; for 1h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction; | 99% |
7-methyl-1H-indole
ethyl 5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate
ethyl (R)-5-methyl-3-(7-methyl-1H-indol-3-yl)-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate
Conditions | Yield |
---|---|
With C38H33O4P In toluene at -78℃; for 5h; enantioselective reaction; | 99% |
pyrrolidine
7-methyl-1H-indole
4-cyanobenzaldehyde
4-((7-methyl-1H-indol-3-yl)(pyrrolidin-1-yl)methyl)benzonitrile
Conditions | Yield |
---|---|
In methanol at 30℃; for 72h; | 99% |
7-methyl-1H-indole
celastrol
Conditions | Yield |
---|---|
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube; | 99% |
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; |
7-methyl-1H-indole
(2-nitroethenyl)benzene
7-methyl-3-(2-nitro-1-phenylethyl)-1H-indole
Conditions | Yield |
---|---|
With 2,6-bis(2,2-dimethylpropionylamino)benzoic acid In chloroform at 40℃; for 24h; Friedel-Crafts Alkylation; | 99% |
7-methyl-1H-indole
ammonium thiocyanate
7-methyl-3-thiocyanato-1H-indole
Conditions | Yield |
---|---|
With oxygen In tetrahydrofuran at 25℃; under 750.075 Torr; for 7h; Irradiation; | 99% |
With copper(II) choride dihydrate; oxygen In ethanol at 20℃; for 24h; Irradiation; | 93% |
With TiO2/MoS2 In acetonitrile at 20℃; for 16h; Irradiation; | 90% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; | 99% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With (R)-2,6-bis(naphthalen-2-yl)-4-oxo-3,5-dioxa-4λ5-phosphacyclohepta[2,1-a;3,4-a']dinapthalen-4-ol In 1,2-dichloro-ethane at 20℃; for 16h; enantioselective reaction; | 99% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With (R)-2,6-bis(naphthalen-2-yl)-4-oxo-3,5-dioxa-4λ5-phosphacyclohepta[2,1-a;3,4-a']dinapthalen-4-ol In 1,2-dichloro-ethane at 20℃; for 16h; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With oxygen In tetrahydrofuran at 20℃; under 760.051 Torr; Irradiation; | 99% |
With iridium(III) bis[2-(4,6-difluorophenyl)pyridinato]picolinate In acetonitrile at 25℃; Irradiation; Green chemistry; | 90% |
With iridium(III) bis[2-(4,6-difluorophenyl)pyridinato]picolinate In acetonitrile at 20℃; Irradiation; Green chemistry; | 90% |
With 3-chloro-benzenecarboperoxoic acid; sodium bromide In acetonitrile at 20℃; for 24h; regioselective reaction; | 61% |
Conditions | Yield |
---|---|
With cerium(III) chloride; silver(l) oxide In 1,2-dichloro-ethane at 20℃; Darkness; | 99% |
7-methyl-1H-indole
ethyl 3,3,3-trifluoro-2-iminopropionate
ethyl (S)-2-amino-3,3,3-trifluoro-2-(7-methyl-1H-indol-3-yl)propanoate
Conditions | Yield |
---|---|
With (S)-3-(anthracen-9-yl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate In chloroform at -60℃; for 1h; Inert atmosphere; enantioselective reaction; | 99% |
7-methyl-1H-indole
N-(4-bromobenzylidene)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With (Rp)-4,12-di(4-(3',5'-bis(trifluoromethyl))-phenyl-3-yl)-[2.2]paracyclophane-hydrogenphosphate In toluene at -20℃; for 12h; Molecular sieve; enantioselective reaction; | 99% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With (11aR)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In toluene at 60℃; for 3h; enantioselective reaction; | 99% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With C55H51F3N4O3PdS In toluene at 40℃; Inert atmosphere; Alkaline conditions; enantioselective reaction; | 99% |
7-methyl-1H-indole
9-phenyl-fluoren-9-ol
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 60℃; for 4h; Sealed tube; | 99% |
7-methyl-1H-indole
Conditions | Yield |
---|---|
With Diphenylphosphinic chloride In acetonitrile at 60℃; for 1h; Schlenk technique; Inert atmosphere; | 99% |
7-Methylindole is used in the production of agricultural chemicals and pharmaceuticals.
7-Methylindole is used for organic synthetic reagent.
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