Sodium hydride → HCID 18518630, compound

HRID 1369125Notes

Reaction equation

HRID 1369125 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.[H-].[Na+].[Si:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]I)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].OS([O-])(=O)=O.[K+]>O>[Si:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:6]1[C:7]2[C:3](=[C:2]([Br:1])[CH:10]=[C:9]([I:11])[CH:8]=2)[C:4](=[O:13])[C:5]1=[O:12])([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 14567006tert-Butyl[(5-iodopentyl)oxy]dimethylsilaneHCID 18518602HCID 18518602, compound

Product 1

HCID 18518630HCID 18518630, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-bromo-6-iodoisatin (450 mg, 1.32 mmol) and 60% NaH (60 mg, 1.5 mmol) was added 5-t-butyldimethylsilyloxy-1-iodopentane (600 mg, 1.83 mmol). The mixture was stirred for 4 h at 50° C. and water and 5% KHSO4 was added. The mixture was extracted with toluene-ethyl acetate and the extracts were washed with 5% KHSO4, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 6:1 hexane/ethyl acetate to give the title compound (615 mg, 86%).

Workup

  1. extractionThe mixture was extracted with toluene-ethyl acetate
  2. washthe extracts were washed with 5% KHSO4
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 6:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c7124c157538480d8fcf8ed8dece75f8
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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