Water → 5-Bromo-1-(triisopropylsilyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

Place a 35% oil dispersion of KH (6 g) in a flask under nitrogen, rinse with 50 mL hexanes and dry under vacuum. Cool the solid suspension in 100 mL anhydrous DMF to 0° C. Add dropwise over 10 minutes a solution of 5-bromoindole (10.3 g, 52.5 mmol) in 25 mL DMF. Stir the mixture 1 hour at 0° C. then treat with triisopropylsilyltrifluoromethane sulfonate (32.2 g, 105.1 mmol). Remove the cooling bath and stir the reaction 72 hours before pouring into 500 mL water and extracting with EtOAc. Dilute the combined extracts with hexanes, wash with brine then dry over MgSO4. Concentration under vacuum and chromatograph on silica gel eluting with 1% EtOAc in hexanes to give 5-Bromo-1-triisopropylsilanyl-1H-indole as a colorless oil: 1H NMR (CDCl3) 7.73–7.72 (d, 1H), 7.36–7.34 (d, 1H), 7.24–7.23 (d, 1H), 7.21–7.19 (m, 1H), 6.55–6.54 (m, 1H), 1.72–1.61 (m, 3H, 1.13–1.10 (m, 18H).

Provenance & Evidence