Iodine → HCID 118022085, compound

HRID 518409Notes

Reaction equation

HRID 518409 reaction equation
[CH2:1]([S:3]([C:6]1[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[I:13]I>C1COCC1.O>[CH2:1]([S:3]([C:6]1[N:11]=[C:10]([I:13])[C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5])[CH3:2].[CH2:1]([S:3]([C:6]1[N:11]=[CH:10][C:9]([OH:12])=[C:8]([I:13])[CH:7]=1)(=[O:4])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 807IodineHCID 231454076-(Ethanesulfonyl)pyridin-3-ol

Product 2

HCID 118022085HCID 118022085, compoundHCID 118022404HCID 118022404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound from Step 4 (3 g, 16 mmol) in a mixture of THF (20 mL) and H2O (20 mL) was added KI (662 mg, 4 mmol) and iodine (6.1 g, 24 mmol). The reaction was stirred at rt for 1 hour and then heated to 60° C. for another 17 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure to remove the THF. The mixture was diluted with water (100 mL) and extracted with DCM (10 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC to afford 6-ethylsulfonyl-2-iodopyridin-3-ol and 6-ethylsulfonyl-4-iodopyridin-3-ol as white solids. 6-ethylsulfonyl-2-iodopyridin-3-ol: 1H NMR (DMSO-d6, 400 MHz) δ 7.85 (d, J=8.4 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 3.30 (q, J=7.2 Hz, 2H), 1.11 (t, J=7.2 Hz 3H). LCMS: 313.8 (M+1)+; 6-ethylsulfonyl-4-iodopyridin-3-ol: 1H NMR (DMSO-d6, 400 MHz) δ 8.23 (s, 1H), 8.18 (s, 1H), 3.31 (q, J=7.2 Hz, 2H, overlapped with solvent peak), 1.10 (t, J=7.2 Hz 3H). LCMS: 313.8 (M+1)+

Workup

  1. temperatureheated to 60° C. for another 17 hours
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customto remove the THF
  5. additionThe mixture was diluted with water (100 mL)
  6. extractionextracted with DCM (10 mL×3)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-6ee713fbff934780a9c52b5d91f949f9
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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