Methyl iodide → 1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indole

HRID 1767935Notes

Reaction equation

[C:1]([Li])(C)(C)C.CCCCC.Br[C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:18][CH:19]=2)[N:14]([Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH:13]=1.CI>C1COCC1>[C:32]([Si:29]([CH3:31])([CH3:30])[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:16]=2)[C:12]([CH3:1])=[CH:13]1)([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: -78 °C

Procedure

A 1.5 M solution of tert-butyllithium in pentane (3.3 ml, 4.99 mmol) was added dropwise to a solution of 3-bromo-1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (1 g, 2.27 mmol) in THF (6 ml) at −78° C. under an argon atmosphere. After 15 min methyl iodide (0.28 ml, 4.54 mmol) was added at −78° C. The reaction mixture was stirred for another 30 min at −78° C. and then for 2 h at RT. After quenching with saturated aqueous NaHCO3 solution the reaction mixture was partitioned between ether and water. The ether phase was dried over sodium sulfate and concentrated in vacuo to give 863 mg (2.3 mmol, quant.) 1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indole as red crystals.

Workup

waitfor 2 h at RT
customAfter quenching with saturated aqueous NaHCO3 solution the reaction mixture
customwas partitioned between ether and water
dry with materialThe ether phase was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d792a87734534d2095acc9b9ff17ab93
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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