反应详情

To a mixture of 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (500 mg, 1.04 mmol) and 3-bromomandelic acid (288 mg, 1.25 mmol) in a 20 mL microwave reaction flask was added THF (3 mL), acetonitrile (3 mL) and sodium carbonate (3 mL, 1 N aqueous solution, 3 mmol). The mixture was purged with nitrogen for 1 min. dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (73 mg, 89 μmol) was added and the purging continued for another minute. The flask was sealed and irradiated in a microwave reactor to 120° C. for 20 min. The reaction mixture was partitioned between aqueous saturated sodium chloride and ethyl acetate (15 mL:15 mL). The aqueous layer was extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford hydroxy-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-acetic acid as a yellow solid (370 mg, 67% yield). MS: m/z 506 (M+H+).

1. customin a 20 mL microwave reaction flask
2. additionwas added
3. customThe flask was sealed
4. customirradiated in a microwave reactor to 120° C. for 20 min
5. customThe reaction mixture was partitioned between aqueous saturated sodium chloride and ethyl acetate (15 mL:15 mL)
6. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×2)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over sodium sulfate
9. customevaporated
10. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane