Reaktionsgleichung
[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]=1Komponenten
Versuchsvorschrift
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).
Aufarbeitung
- extractionthe mixture was extracted with EtOAc (100 mL×3)
- washThe combined organic layers were washed with brine (100 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by preparative HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-ff489caa19fe43b7a7c3ba3fab29c59a
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09034900B2
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