6-Methoxy-2-phenylimidazo[1,2-a]pyridine synthesis

9synthesis methods

Product Name:6-Methoxy-2-phenylimidazo[1,2-a]pyridine
CAS Number:869583-76-6
Molecular formula:C14H12N2O
Molecular Weight:224.26

100-41-4
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10167-97-2 Synthesis

10167-97-2
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6-Methoxy-2-phenylimidazo[1,2-a]pyridine

869583-76-6
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Yield:869583-76-6 80%

Reaction Conditions:

Stage #1: ethylbenzenewith N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in water;ethyl acetate at 65; for 1.5 h;
Stage #2: 2-amino-5-methoxypyridinewith sodium carbonate in water at 80;

Steps:

3.2.1. General Procedure for the Synthesis of Nitrogen-Containing Heterocycles

General procedure: Synthesis of 3a is representative. To a solution of ethylbenzene (1a, 1 mmol, 107 mg) in ethylacetate:water (5:1, 6 mL) were added NBS (3.5 mmol, 628 mg) and AIBN (0.1 mmol, 16.5 mg) at roomtemperature, and the mixture was stirred at 65 °C for 1.5 h. The mixture was concentrated to drynessand then dissolved in water (5 mL), followed by reaction with 2-aminopyridine (2a, 1.2 mmol, 114 mg)and sodium carbonate (5 mmol, 534 mg) for 2 h at 80 °C. After completion of the reaction (as indicatedby TLC), the crude product was extracted with ethyl acetate (3 x 10 mL). The combined organic layerwas dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified bysilica gel column chromatography (PE/EA = 8/1-4/1, v/v) to give 3a (78% yield) as a white solid.

References:

Chen, Liang;Zhu, Huajian;Wang, Jiang;Liu, Hong [Molecules,2019,vol. 24,# 5,art. no. 893]

67-56-1 Synthesis