反应详情

温度

-30 °C

To a solution of (5-bromo-1H-indol-3-yl)-acetic acid (1 g, 3.94 mmol) in THF (66 mL) at −78° C. is added tert-butyl lithium (1.7 M in pentane, 11.6 mL, 19.7 mmol) dropwise and stirred at −78° C. for 30 minutes at −30° C. for 1 hour. Cooled down to −78° C. again and treated dropwise with triisopropyl borate (4.53 mL, 19.7 mmol). The reaction mixture is allowed to warm to room temperature during 1 hour quenched with 2N hydrochloric acid. This mixture is extracted with ether. The extract is dried over sodium sulfate and concentrate to obtain an oil which is subjected to silica gel chromatography affording 3-carboxymethyl-1H-indol-5-yl boronic acid (185 mg, 20%) as a solid.

1. temperatureCooled down to −78° C. again
2. temperatureto warm to room temperature during 1 hour
3. customquenched with 2N hydrochloric acid
4. extractionThis mixture is extracted with ether
5. dry with materialThe extract is dried over sodium sulfate
6. concentrationconcentrate
7. customto obtain an oil which