2,3-Difluoro-4-iodopyridine → 3-Fluoro-4-iodopyridin-2(1H)-one
Reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([I:9])[CH:5]=[CH:4][N:3]=1.C(O)(=[O:12])C.O>>[F:8][C:7]1[C:2](=[O:12])[NH:3][CH:4]=[CH:5][C:6]=1[I:9]Participants
3
Procedure
2,3-Difluoro-4-iodopyridine (300 mg, 1.24 mmol) was suspended in acetic acid:water (2:1, 15 mL). The mixture was heated to reflux and stirred at this temperature overnight. Reaction was concentrated to dryness, and triturated in water (10 mL) for 30 min. The solid was collected via filtration, washed with water (2×10 mL), and pentane (2×20 mL) and dried under vacuum to afford the title compound as a white solid (354 mg, 71.4%). LC-MS m/z 342.0 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 6.56-6.82 (m, 1H) 6.83-7.18 (m, 1H).
Workup
- temperatureThe mixture was heated
- temperatureto reflux
- customReaction
- concentrationwas concentrated to dryness
- customtriturated in water (10 mL) for 30 min
- filtrationThe solid was collected via filtration
- washwashed with water (2×10 mL), and pentane (2×20 mL)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-3c12165df4974b6184087a725aa89169
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664401B2
Reaction notes
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