ChemicalBook CAS DataBase List 5-METHYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

5-METHYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis

4synthesis methods

Product Name:5-METHYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
CAS Number:51135-70-7
Molecular formula:C11H12N2O2
Molecular Weight:204.23

13061-96-6

5-BROMO-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

885276-93-7

5-METHYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

51135-70-7

Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate (1.0 g, 3.73 mmol) and methylboronic acid (448 mg, 7.46 mmol) were used as raw materials, and Pd(dppf)Cl2 (545 mg, 0.746 mmol) and Cs2CO3 (2.42 g, 7.46 mmol) were added, protected by argon gas, in DMF ( 5.0 mL) in DMF. The reaction mixture was stirred at 100 °C for 2 hours. After completion of the reaction, the mixture was concentrated and purified by silica gel column chromatography using petroleum ether: ethyl acetate (5:1, v/v) as eluent to afford the target compound, ethyl 5-methylpyrazolo[1,5-a]pyridine-3-carboxylate, as an orange solid (589 mg, 77% yield).ESI-MS m/z = 204.5 [M + H]+.

13061-96-6
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885276-93-7 Synthesis

885276-93-7
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51135-70-7
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Yield:51135-70-7 77%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;caesium carbonate in N,N-dimethyl-formamide at 100; for 2 h;

Steps:

449.a Example 449 step a:

A solution of ethyl 5-bromopyrazolo[1,5-ajpyridine-3-carboxylate (1.0 g, 3.73 mmol),methylboronic acid (448 mg, 7.46 mmol), Pd(dppf)C12 (545 mg, 0.746 mmol) and C52CO3(2.42 g, 7.46 mmol) was dissolved in DMF (5.0 mL), then the mixture was stirred at 100 °Cfor two hours. It was concentrated, and purified by silica gel chromatography with PE:EA=5: 1to obtain the desired compound as an orange solid (589 mg, 77%). ESI MS m/z = 204.5[M+Hj.

References:

WO2017/15449,2017,A1 Location in patent:Page/Page column 342