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81803-60-3

81803-60-3 Structure

81803-60-3 Structure
IdentificationBack Directory
[Name]

ETHYL IMIDAZO[1,5-A]PYRIDINE-3-CARBOXYLATE
[CAS]

81803-60-3
[Synonyms]

ethyl imidazo(1,5)-pyridine-3-carboxylate
ETHYL IMIDAZO[1,5-A]PYRIDINE-3-CARBOXYLATE
ethyl 1H-imidazo[1,5-a]pyridine-3-carboxylate
Imidazo[1,5-a]pyridine-3-carboxylic acid ethyl ester
[Molecular Formula]

C10H10N2O2
[MDL Number]

MFCD10697855
[MOL File]

81803-60-3.mol
[Molecular Weight]

190.2
Chemical PropertiesBack Directory
[density ]

1.22±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

3.98±0.30(Predicted)
[Appearance]

Light yellow to yellow Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Spectrum DetailBack Directory
[Spectrum Detail]

ETHYL IMIDAZO[1,5-A]PYRIDINE-3-CARBOXYLATE(81803-60-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

ethyl 2-oxo-2-(pyridin-2-ylmethylamino)acetate

46460-25-7

ETHYL IMIDAZO[1,5-A]PYRIDINE-3-CARBOXYLATE

81803-60-3

General procedure for the synthesis of ethyl imidazo[1,5-a]pyridine-3-carboxylate from ethyl 2-oxo-2-((pyridin-2-ylmethyl)amino)acetate: ethyl [(pyridin-2-ylmethyl)carbamoyl]formate (1.00 g, 4.80 mmol, 1.00 equiv) and phosphorus pentoxide (3.41 g, 24.02 mmol, 5.00 equiv) were dissolved in phosphoryl chloride (30 mL). ) were dissolved in phosphoryl chloride (30 mL) and the reaction was stirred at 110°C for 5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1, v/v) as eluent. 635 mg (70% yield) of the target product, ethyl imidazo[1,5-a]pyridine-3-carboxylate, was finally obtained as a yellow solid.LC-MS (ESI, m/z): 191 [M + H]+.

[References]

[1] Patent: WO2015/25025, 2015, A1. Location in patent: Page/Page column 411; 412
[2] Patent: WO2008/85302, 2008, A1. Location in patent: Page/Page column 96
[3] Organic Letters, 2013, vol. 15, # 9, p. 2290 - 2293
[4] Synthesis (Germany), 2016, vol. 48, # 23, p. 4269 - 4277
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