反应详情

To a stirred solution of ethyl 4-iodo-5-methyl-1H-pyrazole-3-carboxylate (Step 1.1) (7.60 g, 27.1 mmol) in DMF (50 mL) under Ar was added NaH (1.302 g, 32.6 mmol) at 0° C. After 15 min, 4-methoxyphenyl chloride (3.70 mL, 27.1 mmol) was added. The reaction mixture was stirred for 1 hr at rt, quenched with a saturated aqueous solution of NaHCO3 (100 mL) and extracted with EtOAc (100 mL). The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL), dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The crude material was purified by silica gel column chromatography (hexane/EtOAc 5-40%) to afford the title product (6.23 g, 15.57 mmol, 57% yield) as a colorless oil. tR: 5.24 min (HPLC 1); tR: 1.12 min (LC-MS 2); ESI-MS: 401 [M+H]+ (LC-MS 2); Rf=0.66 (hexane/EtOAc 1:1).

1. customquenched with a saturated aqueous solution of NaHCO3 (100 mL)
2. extractionextracted with EtOAc (100 mL)
3. washThe combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL)
4. dry with materialdried over Na2SO4
5. customthe solvent was evaporated off under reduced pressure
6. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 5-40%)