Trimethylsilyl iodide → HCID 18630068, compound

HRID 378071Notes

Reaction equation

HRID 378071 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:4]=[CH:5][C:6]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[C:7]([CH:20]=1)[C:8]([N:10](CC)[CH:11](OC)[C:12](C)(C)C)=[O:9].I[Si](C)(C)C>C(Cl)Cl>[CH3:25][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([Si:21]([CH3:23])([CH3:22])[CH3:24])=[C:7]([CH:20]=1)[C:8]([NH:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 18630141HCID 18630141, compound

Product 1

HCID 18630068HCID 18630068, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 222 (0.31 g, 0.85 mmol) was dissolved in CH2Cl2 (20 mL) and was treated with iodotrimethylsilane (2.1 mL, 15 mmol) in a foil-covered flask. The reaction was stirred for 2 h and was quenched with sat NaHCO3. The mixture was extracted with ether, the organic layers were washed with brine and sat sodium bisulfite, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by RC (ethyl acetate/hexanes) and recrystallized from hexanes to afford 68 mg (5%) of the title compound as a white solid. m.p. 141-143° C.

Workup

  1. customwas quenched with sat NaHCO3
  2. extractionThe mixture was extracted with ether
  3. washthe organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2bbd859357c14b2c9bc9f53ec7c3a4ce
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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