Trimethylsilyl iodide → HCID 18630068, compound

HRID 610963Notes

Reaction equation

HRID 610963 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-17ab26b1259a4f5e8e67ad64ca104dec
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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