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Basic Information
CAS No.: 1060812-84-1
Name: 5-Bromopyrazolo[1,5-a]pyridine
Article Data: 8
Molecular Structure:
Molecular Structure of 1060812-84-1 (5-Bromopyrazolo[1,5-a]pyridine)
Formula: C7H5BrN2
Molecular Weight: 197.034
Synonyms: 5-broMopyrazolo[1,5-a]pyridine;Pyrazolo[1,5-a]pyridine, 5-bromo-;1,3-Benzodioxole-5-carboxaldehyde,8-methoxy-;5-Bromopyrazolo[1,5-a]pyridine(1060812-84-1)
Density: 1.69±0.1 g/cm3(Predicted)
PSA: 17.30000
LogP: 2.09680
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Synthetic route
885276-93-7

ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 4h;99.5%
Stage #1: ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate With sulfuric acid; water for 18h; Reflux;
Stage #2: With sodium hydroxide In water pH=7;		96%
With sulfuric acid In water at 110℃; for 16h;60%
1101120-33-5

5-((tert-butoxycarbonyl)amino)pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 18 h / 20 °C
2.1: hydrogen bromide; sodium nitrite / water / 0.25 h / 0 °C
2.2: 0.25 h / 50 °C
2.3: pH 5
3.1: sulfuric acid; water / 18 h / Reflux
3.2: pH 7
View Scheme

ethyl 5-aminopyrazolo[1,5-a]pyridine-3-carboxylate trifluoroacetate

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogen bromide; sodium nitrite / water / 0.25 h / 0 °C
1.2: 0.25 h / 50 °C
1.3: pH 5
2.1: sulfuric acid; water / 18 h / Reflux
2.2: pH 7
View Scheme
98400-69-2

N-(4-pyridyl) t-butyl carbamate

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: O-(2,4-dinitrophenyl)hydroxylamine / acetonitrile / 18 h / 40 °C
1.2: 18 h / 20 °C
2.1: dichloromethane / 18 h / 20 °C
3.1: hydrogen bromide; sodium nitrite / water / 0.25 h / 0 °C
3.2: 0.25 h / 50 °C
3.3: pH 5
4.1: sulfuric acid; water / 18 h / Reflux
4.2: pH 7
View Scheme
1533440-88-8

1-amino-4-bromopyridin-1-ium iodide

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h
2: sulfuric acid / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
2: sulfuric acid / 80 °C
View Scheme
1120-87-2

4-bromopyridin

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: mesitylenesulfonylhydroxylamine / N,N-dimethyl-formamide / 16 h / 0 - 40 °C
1.2: 6 h / 0 - 20 °C
2.1: sulfuric acid / water / 16 h / 110 °C
View Scheme
1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

3724-43-4, 149409-22-3

Vilsmeier reagent

1101120-53-9

5-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde

Conditions
ConditionsYield
In dichloromethane at 44℃;100%
1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

1352881-82-3

5-bromo-3-iodopyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
With N-iodo-succinimide In methanol at -10 - 20℃; for 18.5h;97.5%
With N-iodo-succinimide In acetonitrile at 20℃; for 16h;96%
With N-iodo-succinimide In acetonitrile at 20℃; for 1h;89%
1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

68-12-2, 33513-42-7

N,N-dimethyl-formamide

1101120-53-9

5-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromopyrazolo[1,5-a]pyridine; N,N-dimethyl-formamide With trichlorophosphate at 20℃; for 2h; Vilsmeier formylation; Inert atmosphere;
Stage #2: With sodium hydroxide In water pH=10;		96%
355836-10-1

2-methoxy-4-trifluoromethoxybenzeneboronic acid

1060812-84-1

5-bromopyrazolo[1,5-a]pyridine

5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyridine

Conditions
ConditionsYield
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium In 1,4-dioxane; water at 80℃; for 16h;85%
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