2,5-dibromo-3-nitro-pyridine
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran at 80℃; Suzuki Coupling; Inert atmosphere; Sealed tube; | 78% |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
6-chloro-2-methoxypyridine
Conditions | Yield |
---|---|
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 3h; Microwave irradiation; Green chemistry; | 72% |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; | 55% |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
6-chloro-3-iodo-2-methoxypyridine
Conditions | Yield |
---|---|
With N-iodo-succinimide at 90℃; for 0.0833333h; Microwave irradiation; | 51% |
(S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester
(6-chloro-2-methoxypyridin-3-yl)boronic acid
C18H23ClN4O3
Conditions | Yield |
---|---|
Stage #1: (S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane at 100℃; for 0.0833333h; Inert atmosphere; Stage #2: (6-chloro-2-methoxypyridin-3-yl)boronic acid With potassium carbonate In 1,2-dimethoxyethane; water for 1.16667h; | |
Stage #1: (S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester; palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,2-dimethoxyethane at 100℃; for 0.0833333h; Inert atmosphere; Stage #2: (6-chloro-2-methoxypyridin-3-yl)boronic acid With potassium acetate In 1,2-dimethoxyethane; water for 1.16667h; Inert atmosphere; |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water / toluene / 3 h / 90 °C / Microwave irradiation; Green chemistry 2: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water-d2 / toluene; tetrahydrofuran / 2 h / 90 °C / Microwave irradiation View Scheme |
(S)-2-(4-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester
(6-chloro-2-methoxypyridin-3-yl)boronic acid
C18H23ClN4O3
Conditions | Yield |
---|---|
Stage #1: (S)-2-(4-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,2-dimethoxyethane at 100℃; for 0.0833333h; Inert atmosphere; Stage #2: (6-chloro-2-methoxypyridin-3-yl)boronic acid With potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 1.16667h; |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
With pyridine; copper diacetate In acetonitrile for 6h; Molecular sieve; Reflux; | 0.075 g |
With pyridine; copper diacetate In acetonitrile for 6h; Molecular sieve; Reflux; | 0.075 g |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper diacetate; pyridine / acetonitrile / 6 h / Molecular sieve; Reflux 2: Lawessons reagent / toluene / 5 h / Reflux View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper diacetate; pyridine / acetonitrile / 6 h / Molecular sieve; Reflux 2: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4: triphenylphosphine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4.1: triphenylphosphine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 5.2: 1.5 h View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4.1: triphenylphosphine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 100 °C / Inert atmosphere; Sealed tube 5.2: 1.5 h 6.1: cerium(III) chloride / tetrahydrofuran / 0.02 h / 20 °C 6.2: 0.17 h View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4: triphenylphosphine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 5: triethylamine / 0.5 h / Microwave irradiation View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: triphenylphosphine; triethylamine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 5: copper(II) bis(trifluoromethanesulfonate); N,N`-dimethylethylenediamine / dimethyl sulfoxide / 4 h / 100 °C / Inert atmosphere; Sealed tube View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: triphenylphosphine; triethylamine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 5: palladium diacetate; ruphos; sodium t-butanolate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere; Sealed tube View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4.1: di-isopropyl azodicarboxylate; triphenylphosphine; triethylamine / dichloromethane / 0 - 20 °C 5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: triphenylphosphine; triethylamine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 0 - 20 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: triphenylphosphine; triethylamine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4: di-isopropyl azodicarboxylate; triphenylphosphine; triethylamine / dichloromethane / 0 - 20 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 1 h / 150 °C / Inert atmosphere 3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere; Sealed tube 4.1: di-isopropyl azodicarboxylate; triphenylphosphine; triethylamine / dichloromethane / 0 - 20 °C 5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.2: 2 h / 20 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 90 °C 3: hydrogenchloride / 1,4-dioxane / 0.33 h / 20 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 90 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 90 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 90 °C 3: hydrogenchloride / 1,4-dioxane / 2 h / 60 °C View Scheme |
(6-chloro-2-methoxypyridin-3-yl)boronic acid
Conditions | Yield |
---|---|
With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In tetrahydrofuran; water at 20 - 60℃; for 2h; |
The CAS registry number of 6-Chloro-2-methoxypyridine-3-boronic acid is 1072946-50-9. Its molecular formula is C6H7BClNO3 and molecular weight is 187.38868. Its systematic name is called (6-Chloro-2-methoxy-3-pyridyl)boronic acid.
Physical properties about 6-Chloro-2-methoxypyridine-3-boronic acid are: (1)ACD/LogP: 1.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.282; (4)ACD/BCF (pH 5.5): 5.082; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 100.438; (7)ACD/KOC (pH 7.4): 4.024; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.546; (12)Molar Refractivity: 42.279 cm3; (13)Molar Volume: 133.589 cm3; (14)Surface Tension: 54.525 dyne/cm; (15)Density: 1.403 g/cm3; (16)Flash Point: 168.172 °C; (17)Enthalpy of Vaporization: 63.261 kJ/mol; (18)Boiling Point: 354.461 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: B(c1ccc(nc1OC)Cl)(O)O
(2)InChI: InChI=1/C6H7BClNO3/c1-12-6-4(7(10)11)2-3-5(8)9-6/h2-3,10-11H,1H3
(3)InChIKey: QMTFZVCHSRMZJW-UHFFFAOYAH
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