3-bromo-2-chloro-5-nitropyridine
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
With hydrogen In tetrahydrofuran at 37℃; under 2250.23 Torr; for 18h; chemoselective reaction; | 92% |
With iron; acetic acid In water for 2h; below 50 deg C; | 87% |
With ammonium chloride; zinc In methanol at 90℃; for 2h; | 70.6% |
3-bromo-2-hydroxy-5-nitropyridine
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / POCl3, quinoline / 2 h / 120 °C 2: 87 percent / Fe, AcOH / H2O / 2 h / below 50 deg C View Scheme |
3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde
2-chloro-3-bromo-5-aminopyridine
5-bromo-6-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 20h; | 97% |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Stage #1: 5-amino-3-bromo-2-chloropyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Sandmeyer Reaction; Stage #2: In water at 0 - 20℃; Sandmeyer Reaction; | 89% |
tri-n-butyl(vinyl)tin
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In 1,4-dioxane for 24h; Reflux; | 89% |
4-vinylpyridine
2-chloro-3-bromo-5-aminopyridine
6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine
Conditions | Yield |
---|---|
With triethylamine; tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 15h; | 84% |
With tris(dibenzylideneacetone)dipalladium (0); triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 15h; |
4-vinylpyridine
2-chloro-3-bromo-5-aminopyridine
tris-(o-tolyl)phosphine
6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine
Conditions | Yield |
---|---|
With triethylamine; tris-(dibenzylideneacetone)dipalladium(0) In ethyl acetate; N,N-dimethyl-formamide | 84% |
2-chloro-3-bromo-5-aminopyridine
N-tert-butyloxycarbonyl-tryptophanal
1,1-dimethylethyl [(1S)-2-[(5-bromo-6-chloro-3-pyridinyl)amino]-1-(1H-indol-3-ylmethyl)ethyl]carbamate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; | 75% |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Stage #1: Phe-COOH With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 2h; Heating / reflux; Stage #2: 5-amino-3-bromo-2-chloropyridine In tetrahydrofuran for 1h; Heating / reflux; | 59.4% |
3-phenyl-propionaldehyde
2-chloro-3-bromo-5-aminopyridine
5-bromo-6-chloro-N-(3-phenylpropyl)-3-pyridinamine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; | 50% |
2-chloro-3-bromo-5-aminopyridine
acetic anhydride
Conditions | Yield |
---|---|
at 20℃; for 1h; | 49.5% |
2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde
2-chloro-3-bromo-5-aminopyridine
5-bromo-6-chloro-N-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 2h; | 45.2% |
5-methylfuran-2-boronic acid
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In 1-methyl-pyrrolidin-2-one; water at 150℃; for 2h; Inert atmosphere; | 22% |
2-chloro-3-bromo-5-aminopyridine
acetic anhydride
5-bromo-6-chloropyridin-3-yl acetate
Conditions | Yield |
---|---|
With tetrafluoroboric acid; sodium nitrite 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h; Yield given. Multistep reaction; |
2-chloro-3-bromo-5-aminopyridine
2-chloro-5-iodo-3-[(E)-2-pyridin-4-ylvinyl]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h 3.1: 9-BBN / 0 - 20 °C 3.2: 40 percent / PdCl2(dppf); Cs2CO3 / dimethylformamide / 8 h / 50 °C 4.1: TFA / CH2Cl2 / 2 h / 20 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: acetic acid / methanol / 3 h / Heating 2.2: Ti(i-PrO)4; NaBH3CN / methanol / 1 h 3.1: TFA / CH2Cl2 / 2 h / 20 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
tert-butyl (1R)-3-{6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1H-indol-3-ylmethyl)propylcarbamate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h 3.1: 9-BBN / 0 - 20 °C 3.2: 40 percent / PdCl2(dppf); Cs2CO3 / dimethylformamide / 8 h / 50 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
[1-{[6-chloro-5-(2-pyridin-4-yl-vinyl)-pyridin-3-ylamino]-methyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: acetic acid / methanol / 3 h / Heating 2.2: Ti(i-PrO)4; NaBH3CN / methanol / 1 h View Scheme |
2-chloro-3-bromo-5-aminopyridine
5-bromo-6-chloropyridin-3-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) HBF4, NaNO2 / 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h 2: 98 percent / 2 N KOH / 0.5 h / 5 °C View Scheme | |
Stage #1: 5-amino-3-bromo-2-chloropyridine With sulfuric acid; sodium nitrite In water at 0 - 25℃; for 0.5h; Stage #2: With acetic acid In water at 100℃; for 12h; |
1-azaadamantane-4-one
2-chloro-3-bromo-5-aminopyridine
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
Stage #1: 1-azaadamantane-4-one; 5-amino-3-bromo-2-chloropyridine With magnesium sulfate; acetic acid for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 14h; Stage #3: toluene-4-sulfonic acid In ethanol; ethyl acetate at -10 - 20℃; Heating / reflux; |
2-chloro-3-bromo-5-aminopyridine
A
(6-chloro-pyridin-3-yl)-(tetrahydro-pyran-4-ylmethyl)-amine
B
2,5'-dichloro-2'-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridin-5-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 40 h / 20 - 120 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C 5: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C 5: triethylamine / dichloromethane / 2 h / 0 - 20 °C 6: tert-butyl alcohol / 5 h / 95 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: potassium carbonate / dimethyl sulfoxide / 9 h / 100 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C View Scheme |
2-chloro-3-bromo-5-aminopyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dimethyl sulfoxide / 3 h / 135 °C View Scheme |
The 5-Amino-3-bromo-2-chloropyridine is an organic compound with the formula C5H4BrClN2. The IUPAC name of this chemical is 5-bromo-6-chloropyridin-3-amine. With the CAS registry number 130284-53-6, it is also named as 2-Chloro-3-bromo-5-aminopyridine. The product's categories are Pyridine; Pyridines; Boronic Acid. In addition, the molecular weight is 207.46.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.98; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 28; (6)ACD/BCF (pH 7.4): 28; (7)ACD/KOC (pH 5.5): 377; (8)ACD/KOC (pH 7.4): 377; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 38.91 Å2; (13)Index of Refraction: 1.648; (14)Molar Refractivity: 41.165 cm3; (15)Molar Volume: 113.073 cm3; (16)Surface Tension: 59.181 dyne/cm; (17)Enthalpy of Vaporization: 57.991 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Exact Mass: 205.924638; (20)MonoIsotopic Mass: 205.924638; (21)Topological Polar Surface Area: 38.9; (22)Heavy Atom Count: 9; (23)Complexity: 101.
People can use the following data to convert to the molecule structure.
1. SMILES:Nc1cnc(Cl)c(Br)c1
2. InChI:InChI=1/C5H4BrClN2/c6-4-1-3(8)2-9-5(4)7/h1-2H,8H2
3. InChIKey:ISKBXMMELYRESC-UHFFFAOYAZ
4. Std. InChI:InChI=1S/C5H4BrClN2/c6-4-1-3(8)2-9-5(4)7/h1-2H,8H2
5. Std. InChIKey:ISKBXMMELYRESC-UHFFFAOYSA-N
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