反应详情

温度

100 °C

A microwave tube was charged with 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-bromo-pyridin-3-ylmethyl)-amide (650 mg, 1.5 mmol), copper(II) triflate (550 mg, 1.5 mmol) and sodium methanesulfinate (230 mg, 2.3 mmol). The flask was sealed, evacuated and purged (3 times) with nitrogen. The solids were taken up in DMSO (5 mL) and N,N′-dimethylethylene diamine (0.490 mL, 4.59 mmol) was added. The solution was stirred at 100° C. After 16 hours, the mixture was diluted with EtOAc (10 mL) and washed with saturated aqueous NH4Cl (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL). The organic layer was dried over MgSO4, filtered through diatomaceous earth and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-80% ethyl acetate in hexanes. Fractions containing the product were pooled and further purified by silica gel chromatography eluting with a gradient of 0-60% ethyl acetate in hexanes. Desired fractions were pooled and concentrated, and the solid was triturated with hexanes (10 mL) to afford the title compound as a white solid.

1. customThe flask was sealed
2. customevacuated
3. custompurged (3 times) with nitrogen
4. washwashed with saturated aqueous NH4Cl (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered through diatomaceous earth
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography
9. washeluting with a gradient of 0-80% ethyl acetate in hexanes
10. additionFractions containing the product
11. customfurther purified by silica gel chromatography
12. washeluting with a gradient of 0-60% ethyl acetate in hexanes
13. concentrationconcentrated
14. customthe solid was triturated with hexanes (10 mL)