ChemicalBook CAS DataBase List METHYL IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLATE

METHYL IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLATE synthesis

6synthesis methods

Product Name:METHYL IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLATE
CAS Number:136117-69-6
Molecular formula:C9H8N2O2
Molecular Weight:176.17

139022-25-6 Synthesis

imidazo[1,2-a]pyridine-6-carboxylic acid

139022-25-6
165 suppliers
$10.00/250mg

74-88-4
353 suppliers
$15.00/10g

METHYL IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLATE

136117-69-6
120 suppliers
$32.00/500mg

Yield: 39%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide

Steps:

62.B B.
B. Imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester Cesium carbonate (15.7 g, 48.2 mmol) and iodomethane (1.50 ml, 24.2 mmol) were added to a solution of imidazo[1,2-a]pyridine-6-carboxylic acid (2.61 g, 16.1 mmol) in DMF (100 ml). The reaction was stirred at ambient temperature overnight, then poured into brine (100 ml) and extracted with ethyl acetate (3*100 mL). The combined organics were washed with saturated sodium bicarbonate solution (25 mL), and a 1N HCl solution (25 mL) then dried over MgSO₄ and evaporated to give imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester as a yellow solid (1.1 g, 39%). ¹H NMR (250 MHz, CDCl₃): δ 8.96 (s, 1H), 7.8-7.6 (m, 4H), 3.98 (s, 3H). MS [EI+] 177 (M+H)⁺.

References:

Gardinier, Kevin M.;Gernert, Douglas J.;Grese, Timothy A.;Neel, David A.;Mapes, Christopher M.;Michellys, Pierre-Yves;Boehm, Marcus F. US2004/167160, 2004, A1

4360-63-8 Synthesis