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, is heated with 1.5 mL of dimethylformamide dimethyl acetal and 100 μL pyrrolidine at 110° C. overnight. The DMF dimethyl acetal is removed in vacuo. The residue is redissolved in 3 mL of acetic acid, hydrazine hydrate (70 μL, 1.38 mmol) is added, and the mixture is heated to 100° C. for 2 h. The acetic acid is removed in vacuo, and the residue is partitioned between EtOAc and saturated NaHCO3. The organic phase is 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 gives a white crystalline powder.

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