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

HRID 1371917Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH:11]([Si:14](OS(C(F)(F)F)(=O)=O)([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:11]([CH3:13])[CH3:12])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

washrinse with 50 mL hexanes
customdry under vacuum
customRemove the cooling bath
stirringstir
customthe reaction 72 hours
extractionextracting with EtOAc
additionDilute the combined extracts with hexanes
washwash with brine
dry with materialthen dry over MgSO4
concentrationConcentration under vacuum and chromatograph on silica gel eluting with 1% EtOAc in hexanes

Sources & evidence

ORD record: ord-61e73751249449dd903cbc3782ec2104
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157488B2

Reaction notes

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