2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In toluene at 110℃; Inert atmosphere; | 94% |
2,3,4,5-tetrahydro-1H-pyrido-[4,3-b]indol-1-one
methyl iodide
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Stage #1: 2,3,4,5-tetrahydro-1H-pyrido-[4,3-b]indol-1-one With sodium hexamethyldisilazane In N,N-dimethyl-formamide at 5℃; for 0.333333h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 5℃; for 0.333333h; | 72% |
2,3,4,5-tetrahydro-1H-pyrido-[4,3-b]indol-1-one
dimethyl sulfate
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone |
5,6-dihydro-4-(2-methyl-2-phenylhydrazino)-2(1H)-pyridinone
sulfuric acid
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In water | |
With sodium hydroxide In water; acetic acid |
N-(4-(2-aminophenyl)but-3-yn-1-yl)-4-methylbenzenesulfonamide
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: pyridine / dichloromethane / 12 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: diethylzinc / toluene; dimethyl sulfoxide / 10 h / 25 °C / 760.05 Torr / Schlenk technique 2.2: 3 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / Schlenk technique; Reflux 4.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 20 °C / Schlenk technique 5.1: sodium anthracenide / 1,2-dimethoxyethane / 1 h / -78 °C / Schlenk technique; Inert atmosphere View Scheme |
2-(4-(N-tosyl)amino-1-butynyl)-N-tosylaniline
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: diethylzinc / toluene; dimethyl sulfoxide / 10 h / 25 °C / 760.05 Torr / Schlenk technique 1.2: 3 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / Schlenk technique; Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 20 °C / Schlenk technique 4.1: sodium anthracenide / 1,2-dimethoxyethane / 1 h / -78 °C / Schlenk technique; Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / Schlenk technique; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 20 °C / Schlenk technique 3: sodium anthracenide / 1,2-dimethoxyethane / 1 h / -78 °C / Schlenk technique; Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 20 °C / Schlenk technique 2: sodium anthracenide / 1,2-dimethoxyethane / 1 h / -78 °C / Schlenk technique; Inert atmosphere View Scheme |
2-iodophenylamine
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / dimethyl sulfoxide / 16 h / 45 °C / Schlenk technique; Inert atmosphere 2.1: pyridine / dichloromethane / 12 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: diethylzinc / toluene; dimethyl sulfoxide / 10 h / 25 °C / 760.05 Torr / Schlenk technique 3.2: 3 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / Schlenk technique; Reflux 5.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 20 °C / Schlenk technique 6.1: sodium anthracenide / 1,2-dimethoxyethane / 1 h / -78 °C / Schlenk technique; Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With sodium anthracenide In 1,2-dimethoxyethane at -78℃; for 1h; Schlenk technique; Inert atmosphere; | 4.6437 g |
2-allyl-phenylamine
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: pyridine / dichloromethane / 20 °C 2.1: dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); silver trifluoromethanesulfonate / toluene / 12 h / 90 °C / Inert atmosphere 3.1: potassium hydroxide / ethanol / 80 °C / Schlenk technique; Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Schlenk technique; Inert atmosphere 4.2: 0 °C / Schlenk technique; Inert atmosphere 5.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 24 h / 20 °C / 3800.26 Torr / Autoclave 6.1: triethylamine / dichloromethane / 20 °C / Schlenk technique 7.1: boron trifluoride diethyl etherate / toluene / 110 °C / Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium hydroxide / ethanol / 80 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 °C / Schlenk technique; Inert atmosphere 3.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 24 h / 20 °C / 3800.26 Torr / Autoclave 4.1: triethylamine / dichloromethane / 20 °C / Schlenk technique 5.1: boron trifluoride diethyl etherate / toluene / 110 °C / Inert atmosphere View Scheme |
N-tosyl-o-allylaniline
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); silver trifluoromethanesulfonate / toluene / 12 h / 90 °C / Inert atmosphere 2.1: potassium hydroxide / ethanol / 80 °C / Schlenk technique; Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Schlenk technique; Inert atmosphere 3.2: 0 °C / Schlenk technique; Inert atmosphere 4.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 24 h / 20 °C / 3800.26 Torr / Autoclave 5.1: triethylamine / dichloromethane / 20 °C / Schlenk technique 6.1: boron trifluoride diethyl etherate / toluene / 110 °C / Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Schlenk technique; Inert atmosphere 1.2: 0 °C / Schlenk technique; Inert atmosphere 2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 24 h / 20 °C / 3800.26 Torr / Autoclave 3.1: triethylamine / dichloromethane / 20 °C / Schlenk technique 4.1: boron trifluoride diethyl etherate / toluene / 110 °C / Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 24 h / 20 °C / 3800.26 Torr / Autoclave 2: triethylamine / dichloromethane / 20 °C / Schlenk technique 3: boron trifluoride diethyl etherate / toluene / 110 °C / Inert atmosphere View Scheme |
2-(1-methyl-indol-2-yl)-ethylamine
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C / Schlenk technique 2: boron trifluoride diethyl etherate / toluene / 110 °C / Inert atmosphere View Scheme |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With methanesulfonic acid In various solvent(s) at 135℃; for 4h; | 74% |
N3-BOC-5-(hydroxymethyl)-4-methylimidazole
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
alosetron
Conditions | Yield |
---|---|
Stage #1: N3-BOC-5-(hydroxymethyl)-4-methylimidazole; 2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one With trifluoroacetic acid In N,N-dimethyl-formamide at 100 - 115℃; Stage #2: With potassium carbonate In water pH=6.8 - 7; Product distribution / selectivity; | 65% |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With methanesulfonic acid In various solvent(s) at 135℃; for 4h; | 62% |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
4(5)-methyl-5(4)-hydroxymethylimidazole
alosetron
Conditions | Yield |
---|---|
With methanesulfonic acid In 1-methyl-pyrrolidin-2-one at 20 - 135℃; for 21h; Schlenk technique; Inert atmosphere; | 58% |
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
With methanesulfonic acid In various solvent(s) at 135℃; for 4h; | 52% |
4-hydroxymethyl-5-methylimidazole hydrochloride
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
alosetron
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 140℃; for 4h; Inert atmosphere; | 29% |
maleic acid
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
2,3,4,5-Tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-6-(phenylmethoxy)-1H-pyrido[4,3-b]indol-1-one maleate
4-hydroxymethyl-5-methylimidazole hydrochloride
sodium hydrogencarbonate
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
alosetron
Conditions | Yield |
---|---|
With p-toluenesulfonic acid monohydrate In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane | |
In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane |
4-chloromethyl-5-methyl-1-tritylimidazole
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
alosetron
Conditions | Yield |
---|---|
With hydrogenchloride In 1,2-dimethoxyethane; water | |
With hydrogenchloride In 1,2-dimethoxyethane; water | |
With hydrogenchloride In 1,2-dimethoxyethane; water |
maleic acid
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
2,3,4,5-Tetrahydro-5-methyl-2-[(2-methyl-1H-imidazol-1yl)methyl]-1H-pyrido[4,3-b]indol-1-one maleate
Conditions | Yield |
---|---|
In ethanol; N,N-dimethyl-formamide |
N3-BOC-5-(hydroxymethyl)-4-methylimidazole
2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / N,N-dimethyl-formamide / 100 - 115 °C 1.2: pH 6.8 - 7 2.1: hydrogenchloride / isopropyl alcohol; methanol / 40 - 45 °C View Scheme |
Following is the structure of 2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (CAS NO.122852-75-9):
Empirical Formula: C12H12N2O
Molecular Weight: 200.2365 g/mol
Molar Refractivity: 57.876 cm3
Molar Volume: 152.137 cm3
Density: 1.316 g/cm3
Flash Point: 261.057 °C
Index of Refraction: 1.686
Surface Tension: 50.375 dyne/cm
Enthalpy of Vaporization of 2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (CAS NO.122852-75-9): 77.828 kJ/mol
Boiling Point of 2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (CAS NO.122852-75-9): 508.047 °C at 760 mmHg
SMILES: O=C3NCCc2c3c1c(cccc1)n2C
InChI: InChI=1/C12H12N2O/c1-14-9-5-3-2-4-8(9)11-10(14)6-7-13-12(11)15/h2-5H,6-7H2,1H3,(H,13,15)
InChIKey: GLHMAFAXJJECMG-UHFFFAOYAH
2,3,4,5-Tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one , its cas register number is 122852-75-9. It also can be called 1H-pyrido[4,3-b]indol-1-one, 2,3,4,5-tetrahydro-5-methyl- ; 5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one .
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