Water → HCID 59418220, compound

HRID 1919362Notes

Reaction equation

HRID 1919362 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14].O>C1COCC1>[C:13]([Si:17]([CH3:19])([CH3:18])[N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

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

Product 1

HCID 59418220HCID 59418220, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-fluoro-1H-indole (30.0 g, 0.222 mol) in anhydrous THF (250 mL) was added sodium hydride (60% suspension in mineral oil, 10.22 g, 0.255 mol) portionwise and maintaining the solution at 0° C. The reaction mixture was stirred at 0° C. for 20 min, then a solution of tert-butyl-chloro-dimethyl-silane (40.15 g, 0.266 mol) in anhydrous THF (20 mL) was added and the solution stirred at RT for 25 h. The reaction mixture was poured into H2O and the layers separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (MgSO4), then concentrated in vacuo. The resultant residue was purified by column chromatography (silica gel, cyclohexane:DCM 100% to 50:50) to provide the title compound as a colourless oil (41.2 g, 74%).

Workup

  1. stirringthe solution stirred at RT for 25 h
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography (silica gel, cyclohexane:DCM 100% to 50:50)

Sources & evidence

ORD record
ord-7884ca68794d4f54b3c71f2756c281ad
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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