反应详情

温度

100 °C

A mixture of 0.144 g (0.479 mmol) of 1-benzyl-5-chloro-3-(hydroxymethyl)cinnolin-4(1H)-one, 0.126 g (0.766 mmol) of mesityl boronic acid, 0.111 g (0.096 mmol) of tetrakis and 0.254 g (1.20 mmol) of potassium phosphate in 8 mL of DMF was heated to 100° C. for 16 h. The reaction mixture was quenched with water and extracted with ethyl acetate containing 5% hexanes. The combined organic layers were washed with brine, dried over sodium sulfate, filtered through a plug of silica gel and concentrated in vacuo onto silica gel. The crude material was purified by flash chromatography eluting with a 25% ethyl acetate/hexanes mixture to give 0.087 g (47%) of the title compound as a tan solid.

1. customThe reaction mixture was quenched with water
2. extractionextracted with ethyl acetate containing 5% hexanes
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered through a plug of silica gel
6. concentrationconcentrated in vacuo onto silica gel
7. customThe crude material was purified by flash chromatography
8. washeluting with a 25% ethyl acetate/hexanes mixture