反应详情

温度

90 °C

A mixture of 2-tert-butyl-5-nitro-1H-indole-4-carbonitrile (200 mg, 0.82 mmol), 2-iodoethanol (77 μL, 0.98 mmol), cesium carbonate (534 mg, 1.64 mmol) and DMF (1.3 mL) was heated to 90° C. overnight. Then more 2-iodoethanol (77 μL, 0.98 mmol) was added and the reaction was stirred at 90° C. for 3 days. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate and then the combined ethyl acetate layers were washed with water (×3) and brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (50-100% CH2Cl2-Hexanes) to yield the product as a yellow solid (180 mg, ˜25% purity by NMR, product co-elutes with the indole starting material). ESI-MS m/z calc. 287.1, found 288.5 (M+1)+. Retention time 1.59 minutes. 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.14 (d, J=9.1 Hz, 1H), 8.02 (d, J=9.1 Hz, 1H), 6.60 (s, 1H), 5.10 (t, J=5.5 Hz, 1H), 4.55 (t, J=6.3 Hz, 2H), 3.78-3.73 (m, 2H) and 1.49 (s, 9H) ppm.

1. customThe reaction mixture was partitioned between ethyl acetate and water
2. washThe aqueous layer was washed with ethyl acetate
3. washthe combined ethyl acetate layers were washed with water (×3) and brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe residue was purified by column chromatography (50-100% CH2Cl2-Hexanes)