反应详情

温度

100 °C

1-(1-Ethyl-6-methoxy-1H-indol-3-yl)-ethanone (100 mg, 0.46 mmol), prepared from 1-ethyl-6-methoxy-1H-indole by the procedure described in example 1L, was heated with 1.5 mL of dimethylformamide dimethyl acetal and 100 μL pyrrolidine at 110° C. overnight. The DMF dimethyl acetal was removed in vacuo. The residue was redissolved in 3 mL of acetic acid, hydrazine hydrate (70 μL, 1.38 mmol) was added, and the mixture was heated to 100° C. for 2 h. The acetic acid was removed in vacuo, and the residue was partitioned between EtOAc and saturated NaHCO3. The organic phase was dried and concentrated and the product purified by silica gel chromatography (EtOAc/Hex, 1/1) to give 59 mg of 1-ethyl-6-methoxy-3-(2H-pyrazol-3-yl)-1H-indole (54%) as a colorless semisolid. Trituration in Et2O gave a white crystalline powder.

1. customThe DMF dimethyl acetal was removed in vacuo
2. dissolutionThe residue was redissolved in 3 mL of acetic acid
3. customThe acetic acid was removed in vacuo
4. customthe residue was partitioned between EtOAc and saturated NaHCO3
5. customThe organic phase was dried
6. concentrationconcentrated
7. customthe product purified by silica gel chromatography (EtOAc/Hex, 1/1)