反应详情

温度

-75 °C

7-Fluoro-1-(triisopropylsilyl)-1H-indole (4.0 g, 14 mmol) (Prepared according to M. Schlosser, et al, Eur. J. Org. Chem. 2006, 2956-2969) was dissolved in 30 mL dry THF, cooled to −75° C., treated in portions with sec-butyl lithium (10 mL, 1.4 M, 14 mmol) and stirred for 2 h at −75° C. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.0 mL, 2.7 g, 14 mmol) was added in portions and the mixture was stirred for 1 h at −75° C. The cooling was removed and the temperature was allowed to rise to 5° C. over 30 min. The reaction was quenched by addition of 5 mL sat. NH4Cl and partitioned between ethyl acetate and water. The organic phase was washed with sat. NaCl, dried (Na2SO4), evaporated onto silica gel, and purified by flash chromatography (SiO2; eluting with hexanes) to give 4.2 g of the title compound as a thick oil (4.2 g, 73%): 1H NMR (400 MHz, CDCl3) δ 7.43 (dd, J=7.9, 4.6 Hz, 1H), 7.38 (m, 2H), 1.75 (m, 3H), 1.38 (s, 12H), 1.13 (d, J=7.6 Hz, 18H). 19F NMR (376 MHz, CDCl3) δ −113.07. EIMS m/z 417.

1. stirringthe mixture was stirred for 1 h at −75° C
2. customThe cooling was removed
3. waitto rise to 5° C. over 30 min
4. customThe reaction was quenched by addition of 5 mL sat. NH4Cl
5. custompartitioned between ethyl acetate and water
6. washThe organic phase was washed with sat. NaCl
7. dry with materialdried (Na2SO4)
8. customevaporated onto silica gel
9. custompurified by flash chromatography (SiO2; eluting with hexanes)