2,3-DIFLUORO-4-IODOPYRIDINE → 3-Fluoro-4-iodopyridin-2(1H)-one

HRID 709268Notes

Reaction equation

HRID 709268 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

Reactant 2

HCID 114478372,3-DIFLUORO-4-IODOPYRIDINEHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 708173253-Fluoro-4-iodopyridin-2(1H)-oneYield 71.4%

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

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customReaction
  4. concentrationwas concentrated to dryness
  5. customtriturated in water (10 mL) for 30 min
  6. filtrationThe solid was collected via filtration
  7. washwashed with water (2×10 mL), and pentane (2×20 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-cce6fe57465f49ada0e5cfc4f4ab1d59
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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