Ethyl iMidazo[1,5-a]pyridine-8-carboxylate

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Ethyl iMidazo[1,5-a]pyridine-8-carboxylate Basic information
Product Name:Ethyl iMidazo[1,5-a]pyridine-8-carboxylate
Synonyms:Ethyl iMidazo[1,5-a]pyridine-8-carboxylate;Imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester;Benzeneethanamine,8-chloro-α-methyl-
CAS:697739-12-1
MF:C10H10N2O2
MW:190.2
EINECS:
Product Categories:
Mol File:697739-12-1.mol
Ethyl iMidazo[1,5-a]pyridine-8-carboxylate Structure
Ethyl iMidazo[1,5-a]pyridine-8-carboxylate Chemical Properties
storage temp. Sealed in dry,Room Temperature
AppearanceLight yellow to yellow Solid
Safety Information
MSDS Information
Ethyl iMidazo[1,5-a]pyridine-8-carboxylate Usage And Synthesis
Synthesis
Formic acid

64-18-6

Ethyl 2-(aminomethyl)nicotinate hydrochloride

697739-11-0

Acetic anhydride

108-24-7

Ethyl iMidazo[1,5-a]pyridine-8-carboxylate

697739-12-1

Acetic anhydride (38.21 mL, 405 mmol) and formic acid (15.28 mL, 405 mmol) were mixed and reacted at 60 °C for 2 h and subsequently cooled to room temperature. To this reaction mixture was added ethyl 2-(aminomethyl)-3-pyridinecarboxylate hydrochloride (17.55 g, 81 mmol), and the resulting mixture was stirred at room temperature for 1 hour and then heated at 35°C for 3 hours. After completion of the reaction, the mixture was cooled to 5 °C and neutralized with 0.88 aqueous ammonia solution, followed by extraction with dichloromethane (3×). The combined dichloromethane layers were washed sequentially with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography to afford ethyl imidazo[1,5-a]pyridine-8-carboxylate (8.67 g, 56% yield) using dichloromethane solution containing 2% methanol (containing 0.5% ammonia) as eluent.

References[1] Patent: WO2004/46133, 2004, A1. Location in patent: Page 32
Ethyl iMidazo[1,5-a]pyridine-8-carboxylate Preparation Products And Raw materials
Raw materialsFormic acid-->Ethyl 2-(aminomethyl)nicotinate hydrochloride-->Acetic anhydride
Tag:Ethyl iMidazo[1,5-a]pyridine-8-carboxylate(697739-12-1) Related Product Information
Methyl imidazo[1,2-a]pyridine-6-carboxylate ethyl iMidazo[1,5-a]pyridine-7-carboxylate ETHYL IMIDAZO[1,5-A]PYRIDINE-3-CARBOXYLATE Imidazo[1,5-a]pyridine-1-carboxaldehyde (9CI) Ethyl 6-broMoisoquinoline-3-carboxylate Imidazo[1,2-a]pyridin-7-ol 6-(Hydroxymethyl)imidazo[1,2-a]pyridine Ethyl iMidazo[1,2-b]pyridazine-3-carboxylic ester IMidazo[1,2-b]pyridazine-3-carboxylic acid IMidazo[1,2-b]pyridazine-3-carbonitrile Imidazo[1,2-b]pyridazin-6-amine 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazine IMIDAZO[1,2-A]PYRIDIN-3-YLMETHANOL IMIDAZO[1,2-A]PYRIDINE-8-CARBOXYLIC ACID Imidazo[1,2-a]pyridin-5-ylamine Imidazo[1,2-a]pyridine-7-carboxylic acid (9CI) IMidazo[1,2-a]pyridine-3-carboxylicacid,Methylester C-IMIDAZO[1,2-A]PYRIDIN-3-YL-METHYLAMINE