Chlorotrimethylsilane → HCID 90046406, compound

HRID 1507559Notes

Reaction equation

HRID 1507559 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20](=[O:24])[C:19]2([CH3:26])[CH3:25].[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>O1CCCC1>[F:13][C:14]1[C:15]([Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20](=[O:24])[C:19]2([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 57439917HCID 57439917, compoundHCID 178418339Butyllithium

Product 1

HCID 90046406HCID 90046406, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of diisopropylamine (5.4 g, 7.6 ml, 52.8 mmol) in dry tetrahydrofuran (23 ml) under an argon atmosphere was cooled to −40° C. and a solution of n-BuLi (1.6 M in hexane, 31.6 ml, 50.5 mmol) was added dropwise. The mixture was stirred at −40° C. for 30 minutes and then added to a solution of 7-fluoro-1,3,3-trimethylindolin-2-one (8.875 g, 45.9 mmol) and trimethylsilyl chloride (5.49 g, 6.46 ml, 50.5 mmol) in dry tetrahydrofuran (69 ml) at −75° C. The reaction mixture was warmed to room temperature within 16 hours. The reaction mixture was carefully quenched with water (2 ml) and diluted with ethyl acetate and water. The aqueous phase was extracted ethyl acetate, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as light yellow oil (8.55 g).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature within 16 hours
  2. customThe reaction mixture was carefully quenched with water (2 ml)
  3. additiondiluted with ethyl acetate and water
  4. extractionThe aqueous phase was extracted ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-8e23e3985add4022ad3c6c0798933c9b
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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