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ChemicalBook CAS DataBase List 5-Pyridin-4-ylthiophene-2-carboxaldehyde 97%
129770-69-0

5-Pyridin-4-ylthiophene-2-carboxaldehyde 97% synthesis

6synthesis methods
4701-17-1 Synthesis
5-Bromothiophene-2-carbaldehyde

4701-17-1
298 suppliers
$6.00/1g

1692-15-5 Synthesis
Pyridine-4-boronic acid

1692-15-5
444 suppliers
$6.00/1g

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Yield:129770-69-0 85%

Reaction Conditions:

with palladium diacetate;sodium carbonate;triphenylphosphine in 1,4-dioxane;water;Inert atmosphere;Reflux;

Steps:

13.5 Example 13-5
Synthesis of Intermediate 13-5: 5-(pyridin-4-yl)thiophene-2-carbaldehyde


Under the protection of nitrogen atmosphere, 5-bromo-2-thiophenecarboxaldehyde (3.80 g, 20.0 mmol), pyridine-4-boronic acid (3.0 g, 24.0 mmol), Na2CO3 (3.18 g, 30.0 mmol), Pd(OAc)2 (224.0 mg, 1.0 mmol) and PPh3 (520.0 mg, 2.0 mmol) were dissolved in the mixed solvent of dioxane and water (v/v=3:1, 80 mL), then refluxed and reacted overnight.
After the reaction was completed, the reaction mixture was cooled to RT, poured into ice-water and extracted with EA.
The combined organic phase was washed with water, dried with Na2SO4.
The crude product was separated by column chromatography to give the desired product (3.2 g, yield 85.0%).

References:

US2020/190066,2020,A1 Location in patent:Paragraph 0270-0271

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