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

HRID 336822Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Li+].CCC[CH2-].[Cl-].[CH:17]([SiH:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])([CH3:19])[CH3:18].O>O1CCCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[Si:20]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 400 mg (2.96 mmol) of 6-fluoroindole dissolved in 6 ml of anhydrous tetrahydrofuran are added dropwise at −78° C. under argon 1.18 ml of a N-butyllithium solution (2.5M in hexane, 2.96 mmol). The reaction mixture is stirred for 5 min at −78° C., then 634 μL (2.96 mmol) of triisopropylsilane chloride are added dropwise at −78° C. to the reaction mixture. This mixture is stirred for 20 min at room temperature then water is added. The product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 99:1) to yield 760 mg (89%) of 6-fluoro-1-triisopropylsilylindole as a colourless oil.

Workup

stirringThis mixture is stirred for 20 min at room temperature
extractionThe product is extracted several times with ethyl acetate
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 99:1)

Sources & evidence

ORD record: ord-29e678f51599486bbcc852ca0df72522
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889711B2

Reaction notes

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