反应详情

温度

110 °C

A mixture of 2-(2-bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (880 mg, 2.2 mmol), 4,4,5,5-tetramethyl-2-(2-methyl-propenyl)-[1,3,2]dioxaborolane (903 μL, 4.4 mmol) and saturated NaHCO3 solution (4.4 mL) in anhydrous DMF (20 mL) is degassed with N2. While under N2 atmosphere, tetrakis(triphenylphosphine)palladium (196 mg, 10 mol %) is added and the reaction is heated in a 110° C. oil bath for 2 h. The reaction is cooled to room temperature, poured into water (40 mL) and extracted with EtOAc (2×30 mL). The combined organic layers are washed with water (15 mL) and brine (20 mL) then concentrated in vacuo. The residue is purified by flash column chromatography (24 g silica gel, gradient elution: 0-50% EtOAc in heptane) to give product (278) as a reddish-brown viscous oil (764 mg, 92%).

1. customis degassed with N2
2. additionWhile under N2 atmosphere, tetrakis(triphenylphosphine)palladium (196 mg, 10 mol %) is added
3. temperatureThe reaction is cooled to room temperature
4. additionpoured into water (40 mL)
5. extractionextracted with EtOAc (2×30 mL)
6. washThe combined organic layers are washed with water (15 mL) and brine (20 mL)
7. concentrationthen concentrated in vacuo
8. customThe residue is purified by flash column chromatography (24 g silica gel, gradient elution: 0-50% EtOAc in heptane)