3-Furoic acid → N-(3-Iodo-4-methylphenyl)furan-3-carboxamide

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-iodo-4-methylphenyl)-3-furamide. LCMS: retention time 3.52 min, MH+328. NMR: δH [2H6]-DMSO 9.92, (1H, b), 8.36, (1H, d), 8.23, (1H, d), 7.80, (1H, t), 7.66, (1H, dd), 7.29, (1H, d), 6.98, (1H, d), 2.33, (3H, s).

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

ORD record

ord-767bb4300369414c91fdf8cfdcaa4e11

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514456B2