3-Furoic acid → N-(3-Iodo-4-methylphenyl)furan-3-carboxamide
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.C1C=CC2N(O)N=NC=2C=1.[I:43][CH2:44][C:45]1[CH:46]=C(C=C[CH:51]=1)N.CC[N:54]([CH:58]([CH3:60])[CH3:59])C(C)C>CN(C=O)C>[I:43][C:44]1[CH:60]=[C:58]([NH:54][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:8])[CH:59]=[CH:51][C:45]=1[CH3:46]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Furoic acid (2.4 g) and HATU (8.15 g) in DMF (25 ml) were stirred at room temperature for 15 min. HOBT (2.9 g), 3-iodomethylaniline (5.0 g) and DIPEA (11.2 ml) were added and the mixture was stirred at room temp for 16 h. The solvent was evaporated under vacuum and the residue was 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 were 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 silica column and eluted with cyclohexane/ethyl acetate (3:1) to give the title compound.
Workup
- customThe solvent was evaporated under vacuum
- customthe residue was partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml)
- extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
- washthe combined organic phases were washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml)
- dry with materialThe organic phase was dried (magnesium sulphate)
- customabsorbed onto silica
- washeluted with cyclohexane/ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-9964be106b8e4859b714f1990aaa29c5
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642276B2
Reaction notes
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