Methanol → HCID 22645140, compound

HRID 1837601Notes

Reaction equation

HRID 1837601 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1I)[C:15]#[N:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][OH:29].[C]=O.CN(C)[CH:34]=[O:35]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15]#[N:16])[CH:17]=[CH:18][C:19]=1[C:28]([O:35][CH3:34])=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11111864t-Butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamateHCID 178418416HCID 178418416, compound

Product 1

HCID 22645140HCID 22645140, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

5 g (12.88 mmol) of 3-(2-(t-butoxycarbonylamino)ethoxy)-4-iodobenzonitrile was dissolved in 60 ml of N,N-dimethylformamide (dehydrated). 3.6 ml (25.8 mmol) of triethylamine, 10 ml (25.8 mmol) of methanol and 145 mg (0.644 mmol) of palladium acetate were added to the obtained solution, and they were stirred in the presence of carbon monoxide at 90° C. for 6 hours. The solvent was evaporated, and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method
  3. customto obtain the crude product, which
  4. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-0c559ca20ebe4a6992c85f0c05860ca9
Source dataset
uspto-grants-2004_08
Patent number
US06784191B2

Reaction notes

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