Trimethylsilyl iodide → HCID 22630912, compound

HRID 2416550Notes

Reaction equation

HRID 2416550 reaction equation
I[Si](C)(C)C.C[O:7]/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>ClCCl>[N:17]1[CH:18]=[CH:19][N:20]=[CH:21][C:16]=1[C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH:8]=[O:7])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 22631197HCID 22631197, compound

Product 1

HCID 22630912HCID 22630912, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodotrimethylsilane (0.46 mL, 3.30 mmol) was added dropwise to a suspension of the product from step A (175 mg, 0.82 mmol) and solid NaHCO3 (100 mg, 1.18 mmol) in dichloromethane (5 mL) at rt. The reaction mixture was stirred at rt for 18 h, carefully quenched with sat. aq. NaHCO3, extracted with dichloromethane, dried with Na2SO4, and concentrated in vacuo to give 110 mg (68%) of the title compound. The product was >95% pure as judged by its 1H NMR spectrum, and was used immediately in the next step without further purification. MS 199 (M+H)+.

Workup

  1. customcarefully quenched with sat. aq. NaHCO3
  2. extractionextracted with dichloromethane
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-026b105e04274616928a52025ae20e2d
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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