Iodoethane → 3-Bromo-2-chloro-5-(ethylsulfonyl)pyridine

HRID 930926

反応式

HRID 930926 の反応式
S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Br:12][C:13]1[C:14]([Cl:23])=[N:15][CH:16]=[C:17]([S:19](Cl)(=[O:21])=[O:20])[CH:18]=1.I[CH2:25][CH3:26]>O>[Br:12][C:13]1[C:14]([Cl:23])=[N:15][CH:16]=[C:17]([S:19]([CH2:25][CH3:26])(=[O:21])=[O:20])[CH:18]=1

参加物

6

反応物 4

HCID 6340IodoethaneHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate2 回HCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

生成物 1

HCID 593265653-Bromo-2-chloro-5-(ethylsulfonyl)pyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

Sodium sulfite (1.755 g, 13.92 mmol) and sodium bicarbonate (1.231 g, 14.65 mmol) were dissolved in water (37 mL) to give a colorless solution. The mixture was heated at 75° C. 3-Bromo-2-chloropyridine-5-sulfonyl chloride (2.132 g, 7.33 mmol) was added portionwise over 1 hour. The reaction mixture was stirred at 75° C. for 1 hour. The mixture was concentrated and N,N-dimethylformamide (13.88 mL) was added. Sodium bicarbonate (1.231 g, 14.65 mmol) and iodoethane (0.589 mL, 7.33 mmol) were added. The resulting mixture was heated to 75° C. for 2 hours and then cooled to ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/heptane) to provide the title compound.

後処理

  1. customto give a colorless solution
  2. concentrationThe mixture was concentrated
  3. additionN,N-dimethylformamide (13.88 mL) was added
  4. temperatureThe resulting mixture was heated to 75° C. for 2 hours
  5. temperaturecooled to ambient temperature
  6. customThe mixture was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-84952ea5e3604f048e593a31dd7ee4df
出典データセット
uspto-grants-2016_03
特許番号
US09296741B2

関連ノート

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