Hexane → 6-fluoro-1-[tris(propan-2-yl)silyl]-1H-indole

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Reaction Steps

Prepared according to: Schlosser, M.; Ginanneschi, A.; Leroux, F. Eur. J. Org. Chem. 2006, 2956-2969. In a 500 mL round bottomed flask, THF (75 mL) was cooled to −78° C. and treated with a butyllithium solution, 1.6 M in hexane (23.12 mL, 37.0 mmol), 6-fluoroindole (5.00 g, 37.0 mmol) and triisopropylsilyl chloride (7.92 mL, 37.0 mmol). The solution was then removed from the cooling bath and warmed to RT and stirred for 1 h. The reaction mixture was concentrated on the rotovap and the crude residue was purified on the ISCO Combiflash Companion (40 g Redisep column, using a gradient of 0-10% EtOAc in hexanes) affording 6-fluoro-1-(triisopropylsilyl)-1H-indole (9.78 g, 33.6 mmol, 91% yield) as a clear, viscous colorless oil. MS (ESI, pos. ion) m/z 292.1 (M+H)+. 1H NMR (400 MHz, CDCl3) δ ppm 7.51 (1H, dd, J=8.4, 5.9 Hz), 7.13-7.23 (2H, m), 6.83-6.92 (1H, m), 6.59 (1H, d, J=2.3 Hz), 1.68 (3H, quin, J=7.5 Hz), 1.14 (18H, d, J=7.6 Hz).

Provenance & Evidence