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Procedure for Synthesis of 6-Chloro-3-
m
-tolyl-imidazo[1,2-
a
]pyridine 2 under Coventional Heating:
A mixture of 3-bromotoluene (0.12 mL, 0.98 mmol), 6-chloroimidazo[1,2-a]pyridine (0.1 g, 0.66 mmol), K2CO3 (0.18 g, 1.3 mmol), PPh3 (0.0073 g, 0.033 mmol) and Pd(OAc)2 (0.017 g, 0.063 mmol) in 1,4-dioxane (2 mL) was heated to 100 °C. The reaction was stirred for 48 h, and then the mixture was cooled to r.t. and extracted with CH2Cl2 (3 ×). The combined organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (EtOAc-PE) to give 6-chloro-3-m-tolylimidazo[1,2-a]pyridine(2) as an oil (146 mg, 92% yield). 1H NMR (250 MHz, CDCl3): δ = 2.45 (s, 3 H, CH3), 7.16 (dd, J = 1.9, 9.4 Hz, 1 H), 7.26 (d, J = 7.5 Hz, 1 H), 7.33 (m, 2 H), 7.43 (t, J = 7.5, 8.2 Hz, 1 H), 7.62 (d, J = 9.4 Hz, 1 H), 7.63 (s, 1 H), 8.34 (d, J = 1.9 Hz, 1 H). 13C NMR (62.5 MHz, CDCl3): δ = 22.1, 119.2, 121.6, 122.0, 125.7, 126.2, 129.2, 129.44 (2 × CH), 129.9 (2 × CH), 130.1, 133.9, 139.9.
24
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25
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Procedure for Synthesis of 6-Chloro-3-
m
-tolyl-imidazo[1,2-
a
]pyridine 2 under Microwave Irradiation: The 6-chloroimidazo[1,2-a]pyridine (0.1 g, 0.66 mmol) was dissolved in 1,4-dioxane-EtOH (1.5 mL; 2:1) in a microwave vial equipped with a stir bar. 3-Bromotoluene (0.12 mL, 0.98 mmol), K2CO3 (0.18 g, 1.3 mmol), PPh3 (0.0073 g, 0.033 mmol) and Pd(OAc)2 (0.017 g, 0.063 mmol) were added under argon and subjected to microwave irradiation for 1 h at 130 °C with stirring. The reaction vessel was allowed to cool to r.t. and was diluted with CH2Cl2 (15 mL). The mixture was extracted with CH2Cl2 (3 ×). The combined organic layer was dried over MgSO4 and concentrated under vacuum. The crude material thus obtained was purified by column chromatography on silica gel (EtOAc-PE) to give 6-chloro-3-m-tolylimidazo[1,2-a]pyridine(2) as an oil (148 mg, 93% yield).
