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Water → 1-(tert-butyldimethylsilyl)-5-fluoro-1H-indole

HRID 2278386
Notes
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Reaction equation

HRID 2278386 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>CN(C=O)C>[Si:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([F:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 678615-Fluoroindole

Product 1

HCID 594182201-(tert-butyldimethylsilyl)-5-fluoro-1H-indoleYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

At 0° C., NaH (1.88 g, 46.2 mmol) was added to a solution of 5-fluoro-1H-indole (5.2 g, 38.5 mmol) in 40 mL DMF. After 10 min at 0° C. tert-butyldimethylsilyl chloride (6.96 g, 46.2 mmol) was added and the mixture allowed to stir at 0° C. for an additional 1 h. The mixture was warmed to room temperature and stirred overnight, then diluted by the addition of water and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography to give the title compound (6.5 g, 67.7%)

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2929674c069a4d4496e51ba67c9d74be
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133180B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes