3-Furoic acid → N-(3-iodomethylphenyl)-3-furamide

HRID 31416

Reaction equation

HRID 31416 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:33]1[CH:34]=[CH:35][C:36]2[N:41](O)N=N[C:37]=2[CH:38]=1.[I:43][C:44]1C=C(C=CC=1C)N.CCN(C(C)C)C(C)C>CN(C=O)C>[I:43][CH2:44][C:34]1[CH:35]=[C:36]([NH:41][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:8])[CH:37]=[CH:38][CH:33]=1

Participants

7

Reactant 5

HCID 102683-Furoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1188893-Iodo-p-toluidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 69320743N-(3-iodomethylphenyl)-3-furamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Furoic acid (2.4 g, 21.45 mmol) and HATU (8.15 g, 21.45 mmol) in DMF (25 ml) were stirred at room temperature for 15 mins. HOBT (2.9 g, 21.45 mmol), 3-iodo-4-methylaniline (5.0 g, 21.45 mmol) and DIPEA (11.2 ml, 64.35 mmol) were added and the reaction stirred at room temperature for 16 hrs. The solvent was evaporated under vacuum and the residue partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml). The aqueous layer was extracted with ethyl acetate (50 ml) and the combined organic phases washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml). The organic phase was dried (magnesium sulphate) and absorbed onto silica. The silica was applied to a flash silica column and eluted with cyclohexane/ethyl acetate (3:1). The solvent was evaporated from the product fractions under vacuum to give N-(3-iodomethylphenyl)-3-furamide.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
  4. washthe combined organic phases washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml)
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. customabsorbed onto silica
  7. washeluted with cyclohexane/ethyl acetate (3:1)
  8. customThe solvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record
ord-28448830e92644b091713eedb7019b67
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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