Trimethylsilyl iodide → HCID 136344264, compound

HRID 1669382Notes

Reaction equation

HRID 1669382 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:28])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20]C(OC(C)(C)C)=O)[CH:15]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:28])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 136344265HCID 136344265, compound

Product 1

HCID 136344264HCID 136344264, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.00 g of 4-hydroxy-3-[3-[3-(tert-butoxycarbonylamino)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 200 ml of chloroform was added 2.96 g of iodotrimethylsilane at room temperature, and this was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was washed with 60 ml of chloroform to obtain 1.64 g of 4-hydroxy-3-[3-(3-aminophenyl)-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone as a yellow crystal.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. washthe residue was washed with 60 ml of chloroform

Sources & evidence

ORD record
ord-8d307dc14be2459ea837f9a377235fcc
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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