Methanol → HCID 22645140, compound

HRID 2414427Notes

Reaction equation

HRID 2414427 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. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. customAfter the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product
  3. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-5399c051dc134d57be945258c3318596
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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