Iodine → 4-Iodo-6-methylsulfonylpyridin-3-ol

HRID 518405Notes

Reaction equation

HRID 518405 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[I:12]I.C([O-])(O)=O.[Na+].O>C1COCC1>[I:12][C:7]1[CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[N:10]=[CH:9][C:8]=1[OH:11].[I:12][C:9]1[C:8]([OH:11])=[CH:7][CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[N:10]=1

Participants

7

Reactant 4

HCID 807IodineHCID 962Water2×HCID 516892Sodium BicarbonateHCID 231451966-(Methylsulfonyl)pyridin-3-ol

Product 2

HCID 1180220244-Iodo-6-methylsulfonylpyridin-3-olHCID 1180223722-Iodo-6-methylsulfonylpyridin-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the title compound from Step 1 (3.0 g, 17.34 mmol), I2 (6.6 g, 26.01 mmol), NaHCO3 (2.2 g, 26.20 mmol) and KI (0.72 g, 4.34 mmol) in THF (30 mL) and H2O (30 mL) was stirred at 60° C. for 18 hrs. Water (100 mL) was added and the mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 4-iodo-6-methylsulfonylpyridin-3-ol (700.0 mg) and 2-iodo-6-methylsulfonylpyridin-3-ol (700.0 mg). 2-iodo-6-methylsulfonylpyridin-3-ol: 1H NMR (CDCl3, 400 MHz) δ 12.08 (brs, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 3.19 (s, 3H). 4-iodo-6-methylsulfonylpyridin-3-ol: 1H NMR (CDCl3, 400 MHz) δ 12.0 (brs, 1H), 8.24 (s, 1H), 8.17 (s, 1H), 3.20 (s, 3H).

Workup

  1. extractionthe mixture was extracted with EtOAc (100 mL×3)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-542ace4993ea452dac80a938285196db
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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