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CAS No.: | 893440-50-1 |
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Name: | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine |
Article Data: | 21 |
Molecular Structure: | |
Formula: | C12H19BN2O3 |
Molecular Weight: | 250.105 |
Synonyms: | 2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyridin-3-ylamine; |
Melting Point: | 131-133℃ |
Solubility: | Slightly soluble in water. |
PSA: | 66.60000 |
LogP: | 1.55280 |
[2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-3-yl]carbamic acid benzyl ester
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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With hydrogen; palladium hydroxide on carbon In methanol at 20℃; for 5h; | 97% |
5-bromo-2-(methyloxy)-3-pyridinamine
bis(pinacol)diborane
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 20 - 100℃; | 95% |
Stage #1: 5-bromo-2-(methyloxy)-3-pyridinamine; bis(pinacol)diborane In 1,4-dioxane for 0.166667h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; | 91.1% |
With 3Na(1+)*C18H12O10PS3(3-); potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 80 - 90℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 86% |
2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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With hydrogen; Raney-Ni In methanol for 2h; | 95% |
With hydrogen In methanol for 2h; | 95% |
With hydrogen; Raney-Ni In methanol at 20℃; for 2h; | 89% |
With hydrogen In methanol at 20℃; for 2h; | 89% |
With palladium on activated charcoal In methanol at 20℃; |
bis(pinacol)diborane
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 70 - 90℃; for 6h; Inert atmosphere; | 84% |
5-bromo-2-methoxy-3-nitropyridine
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: hydrogenchloride; iron / ethanol; water / 23 h / 10 - 25 °C / Industry scale; Inert atmosphere 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate / acetic anhydride / 3 h / Reflux 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 20 - 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 2 h / Reflux 2: hydrogen / methanol / 2 h / 20 °C View Scheme |
5-bromo-2-chloro-3-nitropyridine
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: methanol / 2.75 h / 0 - 10 °C / Industry scale; Inert atmosphere 2: hydrogenchloride; iron / ethanol; water / 23 h / 10 - 25 °C / Industry scale; Inert atmosphere 3: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: methanol / 2.75 h / 0 - 10 °C / Inert atmosphere; Large scale 2: ethanol; iron / 20 - 25 °C / Large scale 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere View Scheme |
bis(pinacol)diborane
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 2 h / Reflux 2: hydrogen / methanol / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: palladium on activated charcoal / methanol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / Reflux 2: hydrogen / Raney-Ni / methanol / 2 h / 20 °C View Scheme |
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C / Industrial scale 2: potassium acetate; 3Na(1+)*C18H12O10PS3(3-); palladium diacetate / N,N-dimethyl-formamide / 20 h / 80 - 90 °C / Inert atmosphere View Scheme |
5-bromo-2-methoxy-nicotinic acid
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: triethylamine; diphenylphosphoranyl azide / 4 h / 10 - 80 °C / Industrial scale 2: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C / Industrial scale 3: potassium acetate; 3Na(1+)*C18H12O10PS3(3-); palladium diacetate / N,N-dimethyl-formamide / 20 h / 80 - 90 °C / Inert atmosphere View Scheme |
2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: triethylamine; 3Na(1+)*C18H12O10PS3(3-) / 4 h / 10 - 80 °C 2: hydrogenchloride / ethyl acetate; methanol / 8 h / 20 - 30 °C 3: potassium acetate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 6 h / 70 - 90 °C / Inert atmosphere View Scheme |