反应详情

温度

100 °C

A mixture of 3-bromo-5-(2-methyl-imidazol-1-ylmethyl)-pyridine (120 mg, 0.48 mmol), bis(triphenylphosphine)palladium (II) choride (10 mg, 0.01 mmol) and KOAc (140 mg, 0.14 mmol) were stirred in dioxane (10 ml) for 1 h at 20° C. 4-Chlorophenyl boronic acid (78 mg, 0.05 mmol) and 2N Na2CO3 solution (1.2 ml) were then added and the mixture heated to 100° C. for 7-24 h under an argon atmosphere. After cooling, the solvent was evaporated and 2N NaOH (5 ml) and AcOEt were added. The mixture was shaken and the aqueous phase separated and further extracted with AcOEt, the combined organic extracts were washed with brine then dried over Na2SO4, filtered and evaporated. The residue was chromatographed [silica, elution with CH2Cl2/(2M NH3 in MeOH)=97:3)]. The product was dissolved in MeOH, cooled to 4° C. with stirring and treated with HCl/EtOH (1.46 M 1.1 eq) for 45 min. Evaporation of the solvent and drying under high vacuum at 50° C. for 2 h afforded the title compound (98 mg, 64%) as a light brown solid. MS: m/e=284.2 (M+H+).

1. temperatureAfter cooling
2. customthe solvent was evaporated
3. addition2N NaOH (5 ml) and AcOEt were added
4. customthe aqueous phase separated
5. extractionfurther extracted with AcOEt
6. washthe combined organic extracts were washed with brine
7. dry with materialthen dried over Na2SO4
8. filtrationfiltered
9. customevaporated
10. customThe residue was chromatographed [
11. washsilica, elution with CH2Cl2/(2M NH3 in MeOH)=97:3)]
12. dissolutionThe product was dissolved in MeOH
13. temperaturecooled to 4° C.
14. stirringwith stirring
15. customEvaporation of the solvent
16. customdrying under high vacuum at 50° C. for 2 h