3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one
o-cyanophenylboronic acid-1,3-propylene glycol ester
[14C]-Perampanel
Conditions | Yield |
---|---|
With caesium carbonate; palladium dichloride In N,N-dimethyl-formamide at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; | 73% |
Stage #1: 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one; o-cyanophenylboronic acid-1,3-propylene glycol ester With copper(l) iodide; potassium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane at 70℃; for 4.5h; Heating / reflux; Stage #2: With ammonia In water at 60℃; for 0.883333h; | |
With potassium carbonate; palladium diacetate; copper(l) iodide; triphenylphosphine In 1,2-dimethoxyethane at 70℃; for 4.5h; Heating / reflux; | |
With copper(l) iodide; potassium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane at 70℃; for 4.5h; Heating / reflux; | |
With tetrakis(triphenylphosphine) palladium(0); triethylamine In dichloromethane at 25 - 30℃; for 12h; Reagent/catalyst; Temperature; Solvent; |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol; dimethyl sulfoxide at 40 - 45℃; for 0.5h; Reagent/catalyst; Solvent; | 72% |
3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one
[14C]-Perampanel
Conditions | Yield |
---|---|
With copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 70 - 95℃; for 5.5h; Suzuki coupling; Inert atmosphere; | 69% |
3-(2-cyanophenyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one
phenylboronic acid
[14C]-Perampanel
Conditions | Yield |
---|---|
With ammonia; triethylamine In dichloromethane; water; ethyl acetate | |
With pyridine; copper(II) acetate monohydrate In acetone at 40 - 45℃; for 7h; | 0.370 g |
3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate
[14C]-Perampanel
Conditions | Yield |
---|---|
In water; acetone at 20 - 75℃; for 18.5h; Heating / reflux; | |
In ethyl acetate at 0 - 50.9℃; for 2h; Heating / reflux; | |
at 110℃; X-irradiation; |
2,5-dibromopyridine
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 3 h / 60 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 3.1: water; hydrogen bromide / 3 h / 110 °C 3.2: pH 11 / Cooling with ice 4.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 5.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 6.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 7 steps 1: sodium methylate / methanol / 0.5 h / Reflux 2: n-butyllithium; Trimethyl borate / tetrahydrofuran / -75.1 - 20 °C / Inert atmosphere 3: potassium carbonate; palladium diacetate; triphenylphosphine / water; 1,2-dimethoxyethane / 5.67 h / Reflux 4: hydrogenchloride / water / 3 h / Reflux 5: copper diacetate; pyridine / N,N-dimethyl-formamide / 20 °C 6: N-Bromosuccinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C 7: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere View Scheme |
2-methoxy-5-bromopyridine
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 2.1: water; hydrogen bromide / 3 h / 110 °C 2.2: pH 11 / Cooling with ice 3.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 5.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1: n-butyllithium; Trimethyl borate / tetrahydrofuran / -75.1 - 20 °C / Inert atmosphere 2: potassium carbonate; palladium diacetate; triphenylphosphine / water; 1,2-dimethoxyethane / 5.67 h / Reflux 3: hydrogenchloride / water / 3 h / Reflux 4: copper diacetate; pyridine / N,N-dimethyl-formamide / 20 °C 5: N-Bromosuccinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C 6: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / Reflux 1.2: 1 h / 25 - 30 °C 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 25 - 30 °C 3.1: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 1 h / 25 - 35 °C 4.1: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 12 h / 25 - 30 °C View Scheme |
5-(2-Pyridyl)-1,2-dihydropyridin-2-one
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 3: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: copper diacetate; pyridine / N,N-dimethyl-formamide / 20 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C 3: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 25 - 30 °C 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 1 h / 25 - 35 °C 3: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 12 h / 25 - 30 °C View Scheme | |
Multi-step reaction with 5 steps 1: copper(II) acetate monohydrate; pyridine / N,N-dimethyl-formamide / 20 - 30 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 25 - 45 °C 3: caesium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 110 - 120 °C 4: hydroxylamine hydrochloride / methanol; water / 3 h / 50 - 55 °C 5: sodium hydroxide; acetic anhydride / 2 h / 100 - 140 °C View Scheme |
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C 2: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 25 - 45 °C 2: caesium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 110 - 120 °C 3: hydroxylamine hydrochloride / methanol; water / 3 h / 50 - 55 °C 4: sodium hydroxide; acetic anhydride / 2 h / 100 - 140 °C View Scheme |
2-tri-n-butylstannylpyridine
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 2.1: water; hydrogen bromide / 3 h / 110 °C 2.2: pH 11 / Cooling with ice 3.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 5.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme |
2-methoxy-5-(pyridin-2-yl)pyridine
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: water; hydrogen bromide / 3 h / 110 °C 1.2: pH 11 / Cooling with ice 2.1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 4.1: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 3 h / Reflux 2: copper diacetate; pyridine / N,N-dimethyl-formamide / 20 °C 3: N-Bromosuccinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C 4: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere View Scheme |
phenylboronic acid
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine; copper diacetate / N,N-dimethyl-formamide / 16 h 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 3: copper(l) iodide; palladium diacetate; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane / 5.5 h / 70 - 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: copper(II) acetate monohydrate; pyridine / N,N-dimethyl-formamide / 20 - 30 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 25 - 45 °C 3: caesium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 110 - 120 °C 4: hydroxylamine hydrochloride / methanol; water / 3 h / 50 - 55 °C 5: sodium hydroxide; acetic anhydride / 2 h / 100 - 140 °C View Scheme |
2-methoxy-pyridine-5-boronic acid
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / water; 1,2-dimethoxyethane / 5.67 h / Reflux 2: hydrogenchloride / water / 3 h / Reflux 3: copper diacetate; pyridine / N,N-dimethyl-formamide / 20 °C 4: N-Bromosuccinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C 5: palladium dichloride; caesium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / ethyl acetate / 2 h / 45 °C 1.2: 0.5 h / 20 - 25 °C 2.1: sodium ethanolate / dimethyl sulfoxide; ethanol / 0.5 h / 40 - 45 °C View Scheme |
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hexafluorophosphate / water; acetonitrile / 0.33 h / 20 °C 2: sodium ethanolate / dimethyl sulfoxide; ethanol / 0.5 h / 40 - 45 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium hexafluorophosphate / water; acetonitrile / 0.33 h / 20 °C 2: caesium carbonate / dimethyl sulfoxide / 3.5 h / 55 - 60 °C 3: copper(II) acetate monohydrate; pyridine / acetone / 7 h / 40 - 45 °C View Scheme |
2-(2-cyanophenyl)acetic acid
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.17 h / 20 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C 2.1: caesium carbonate / dimethyl sulfoxide / 3.5 h / 55 - 60 °C 3.1: copper(II) acetate monohydrate; pyridine / acetone / 7 h / 40 - 45 °C View Scheme |
3-bromo-5-(2-pyridyl)-1,2-dihydropyridin-2-one
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 1 h / 25 - 35 °C 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 12 h / 25 - 30 °C View Scheme |
pyridin-2-ylboronic acid
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / Reflux 1.2: 1 h / 25 - 30 °C 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 25 - 30 °C 3.1: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 1 h / 25 - 35 °C 4.1: tetrakis(triphenylphosphine) palladium(0); triethylamine / dichloromethane / 12 h / 25 - 30 °C View Scheme |
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 2: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 3: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
[14C]-Perampanel
Conditions | Yield |
---|---|
With trichlorophosphate In 1,2-dichloro-ethane at 10 - 70℃; for 1h; | |
With acetic anhydride; sodium hydroxide at 100 - 140℃; for 2h; | 7.5 g |
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -60 °C 1.2: 0.83 h / -60 °C 2.1: toluene; ethyl acetate / 10 h / Reflux 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 4.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 5.1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 6.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
2-(2-bromophenyl)-1,3-dioxolan
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: magnesium; ethylene dibromide; iodine / tetrahydrofuran / 1.67 h / 30 - 65 °C / Reflux 1.2: 1.58 h / -5 - 0 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -60 °C 2.2: 0.83 h / -60 °C 3.1: toluene; ethyl acetate / 10 h / Reflux 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 5.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 6.1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 7.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
2-(2-Hydroxyethyl)pyridine
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: hydrogen bromide / toluene; water / 120 °C 2.1: toluene / 14 h / 120 °C 3.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -60 °C 3.2: 0.83 h / -60 °C 4.1: toluene; ethyl acetate / 10 h / Reflux 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 6.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 7.1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 8.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
2-(2-Bromoethyl)pyridine hydrobromide
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: toluene / 14 h / 120 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -60 °C 2.2: 0.83 h / -60 °C 3.1: toluene; ethyl acetate / 10 h / Reflux 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 5.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 6.1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 7.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
ortho-bromobenzaldehyde
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: toluene / Reflux 2.1: magnesium; ethylene dibromide; iodine / tetrahydrofuran / 1.67 h / 30 - 65 °C / Reflux 2.2: 1.58 h / -5 - 0 °C 3.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -60 °C 3.2: 0.83 h / -60 °C 4.1: toluene; ethyl acetate / 10 h / Reflux 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 6.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 7.1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 8.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
ethyl 2-(2-( 1,3-dioxolan-2-yl)phenyl)-2-oxoacetate
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -60 °C 1.2: 0.83 h / -60 °C 2.1: toluene; ethyl acetate / 10 h / Reflux 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 4.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 5.1: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 6.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: toluene; ethyl acetate / 10 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 3: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 4: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 5: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / Reflux 2: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 60 °C 3: hydroxylamine hydrochloride / dimethyl sulfoxide / 0.5 h / 60 °C 4: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 10 - 70 °C View Scheme |
3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one
[14C]-Perampanel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: caesium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 110 - 120 °C 2: hydroxylamine hydrochloride / methanol; water / 3 h / 50 - 55 °C 3: sodium hydroxide; acetic anhydride / 2 h / 100 - 140 °C View Scheme |
Conditions | Yield |
---|---|
With dmap; bis(1,5-cyclooctadiene)nickel(0); trimethylphosphane In toluene at 130℃; for 12h; Glovebox; Sealed tube; | 87% |
Conditions | Yield |
---|---|
With dmap; bis(1,5-cyclooctadiene)nickel(0); trimethylphosphane In toluene at 130℃; for 14h; Glovebox; Sealed tube; | 25% |
[14C]-Perampanel
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate; acetic anhydride In water; toluene |
[14C]-Perampanel
3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate
Conditions | Yield |
---|---|
With water In acetone at -20 - 40℃; for 19.5h; Product distribution / selectivity; | |
With water In acetone at -20 - 65℃; for 1h; Product distribution / selectivity; Heating / reflux; |
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