Methanol → 5-Formyl-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide
Reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][OH:5].[NH2:6][C:7]1O[C:10]([C:12](OC)=O)=[CH:9][CH:8]=1.F[B-](F)(F)F.F[B-](F)(F)F.[CH3:26][N:27]([CH:29]=[C:30](C=[N+](C)C)C=[N+](C)C)[CH3:28].[OH2:39]>>[CH:1]([C:8]1[CH:9]=[C:10]2[CH:12]=[C:30]([C:29]([N:27]([CH3:28])[CH3:26])=[O:39])[O:5][C:4]2=[N:6][CH:7]=1)=[O:2]Participants
Conditions
- Temperature
- 23 °C
Procedure
A solution of sodium methoxide in methanol (30% w/w, 38 mL, 0.21 mol) was added to a mixture of methyl 5-aminofuran-2-carboxylate (15 g, 0.11 mol) and 2-[(dimethylamino)methylene]-1,3-bis(dimethyliminio)propane bis(tetrafluoroborate)salt (38 g, 0.11 mol) in an oven-dried sealed tube. The resulting mixture was heated at reflux for 1 h, then cooled to 23° C., and diluted carefully with water. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 40% ethyl acetate in petroleum ether to give the title compound. 1H NMR (300 MHz, CDCl3): δ 8.50 (d, 1H, J=2.0 Hz), 8.13 (d, 1H, J=2.0 Hz), 7.40 (s, 1H), 5.58 (s, 1H), 3.43 (s, 3H), 3.13 (s, 3H).
Workup
- customsealed tube
- temperatureThe resulting mixture was heated
- temperatureat reflux for 1 h
- concentrationThe reaction mixture was concentrated
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by flash chromatography on silica gel
- washeluting with 40% ethyl acetate in petroleum ether
Sources & evidence
- ORD record
- ord-0d756fa17e6c46f78066905ea268aec3
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296750B2
Reaction notes
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