反应详情

A solution of 5-iodo-1-methyl-1H-imidazole (250 mg, 1.2 mmol) in dichloromethane (2 mL) at 0° C. was treated with 3M phenylmagnesium bromide in diethyl ether (0.4 mL, 1.2 mmol), stirred for 30 minutes, warmed to room temperature, stirred for 30 minutes, cooled to 0° C. and treated with a solution of Example 52C (150 mg, 1.0 mmol) in dichloromethane (1 mL). The mixture was warmed to room temperature, stirred for 2 days, and quenched with ethyl acetate and saturated ammonium chloride. The aqueous phase was extracted with ethyl acetate (2×100 mL), and the combined organic layers were dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in 1:1 ethyl acetate/diethyl ether, filtered, rinsed with 1:1 ethyl acetate/diethyl ether and dried to provide the desired product. 1H NMR (400 MHz, CD3OD) δ 7.91 (dd, 1H), 7.56 (s, 1H), 7.51 (d, 1H), 7.42-7.38 (m, 1H), 6.42 (s, 1H), 6.28-6.24 (m, 1H), 5.93-5.91 (m, 1H), 3.52 (s, 3H).

1. stirringstirred for 30 minutes
2. temperaturecooled to 0° C.
3. temperatureThe mixture was warmed to room temperature
4. stirringstirred for 2 days
5. customquenched with ethyl acetate and saturated ammonium chloride
6. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL)
7. dry with materialthe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. dissolutionThe concentrate was dissolved in 1:1 ethyl acetate/diethyl ether
11. filtrationfiltered
12. washrinsed with 1:1 ethyl acetate/diethyl ether
13. customdried