Iodine → HCID 118022085、化合物

HRID 518409ノート

反応式

HRID 518409 の反応式
[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]

参加物

6

反応物 2

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

生成物 2

HCID 118022085HCID 118022085、化合物HCID 118022404HCID 118022404、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-6ee713fbff934780a9c52b5d91f949f9
出典データセット
uspto-grants-2015_08
特許番号
US09115114B2

反応ノート

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