Water → HCID 68765433, compound

HRID 1170420Notes

Reaction equation

HRID 1170420 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:11]=[C:10]([I:12])[CH:9]=[C:8]2[C:4]=1[C:5](=[O:14])[C:6](=[O:13])[NH:7]2.[H-].[Na+].[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl.O>CN(C)C=O>[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24][N:7]1[C:8]2[C:4](=[C:3]([C:2]([F:15])([F:1])[F:16])[CH:11]=[C:10]([I:12])[CH:9]=2)[C:5](=[O:14])[C:6]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 99973896-Iodo-4-trifluoromethyl-isatin

Product 1

HCID 68765433HCID 68765433, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-trifluoromethyl-6-iodo-1H-indole-2,3-dione (12.0 g, 35.2 mmol) in N,N-dimethylformamide (120 mL) was cooled to 0° C. under nitrogen, and thereto was added 55% sodium hydride (1.70 g, 39.0 mmol) and the mixture was stirred for 30 minutes. Then, to the reaction solution was added dropwise 2-(trimethylsilyl)-ethoxymethyl chloride (7.00 mL, 39.6 mmol), and the mixture was stirred at room temperature for 5 minutes. To the reaction solution was added water, and the mixture was extracted with ethyl acetate-toluene (1:1) twice, washed with water twice, and then dried over magnesium sulfate, and filtered. The filtrate was evaporated and purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the titled compound (13.7 g, 83%).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 minutes
  2. extractionthe mixture was extracted with ethyl acetate-toluene (1:1) twice
  3. washwashed with water twice
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. custompurified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-d94dd0b6189044029c7546633d3ccca5
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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