ChemicalBook CAS DataBase List N-(5-(4-(hydroxymethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

N-(5-(4-(hydroxymethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide synthesis

4synthesis methods

Product Name:N-(5-(4-(hydroxymethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide
CAS Number:1142936-49-9
Molecular formula:C17H16N4O2
Molecular Weight:308.33

1142943-96-1 Synthesis

cyclopropanecarboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide

1142943-96-1
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59016-93-2
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N-(5-(4-(hydroxymethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

1142936-49-9
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Yield:1142936-49-9 78%

Reaction Conditions:

with palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride;potassium carbonate in 1,4-dioxane;lithium hydroxide monohydrate at 90; for 1 h;Inert atmosphere;

Steps:

3.3.1 Step 3.1 Preparation of Compound 5

N-[5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (Int-1) (1.5 g, 5.34 mmol), [4- (Hydroxymethyl)phenyl]boronic acid (SM3) (1.62 g, 10.67 mmol) and potassium carbonate (2.21 g, 16.01 mmol) were dissolved in dioxane (15 mL) and water (3 mL) 3 times to replace nitrogen, then After adding 1,1-bis(diphenylphosphonium)ferrocene palladium chloride (195 mg, 0.267 mmol), nitrogen was replaced again 3 times and added to 90 degrees and stirred for 1 hour.The reaction mixture was added with water (20 mL) and extracted with ethyl acetate (20 mL×3). The organic phase was washed once with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product, which was subjected to silica gel column chromatography ( Eluent: 2% to 5% methanol/dichloromethane) to give yellow solid N-[5-(4-(hydroxymethyl)phenyl]-[1,2,4]triazole[1,5-a] ]dopyridin-2-yl]cyclopropanecarboxamide (5) (1.4 g, 78% yield).

References:

CN114075188,2022,A Location in patent:Paragraph 0111-0117

1010120-55-4 Synthesis

5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

1010120-55-4
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1142936-49-9
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References

19798-81-3 Synthesis

19798-81-3
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References

Ethyl (6-BroMo-pyridin-2-ylaMino)carbonothioylcarbaMate

1010120-59-8
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References