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

HRID 633553

反応式

HRID 633553 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.CN(C)C=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

7

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収率 53.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

Sodium sulfite (4.94 g, 39.2 mmol) and sodium bicarbonate (3.46 g, 41.2 mmol) in water (100 mL) were heated to 75° C. 3-bromo-2-chloropyridine-5-sulfonyl chloride (6.00 g, 20.6 mmol) was added portionwise over 1 hour. The reaction mixture was stirred at 75° C. for 1 hour after complete addition. The mixture was concentrated under vacuum. N,N-Dimethylformamide (37.5 mL), sodium bicarbonate (3.46 g, 41.2 mmol) and iodoethane (1.658 mL, 20.62 mmol) were added. The resulting mixture was heated to 75° C. for 2 hours then cooled to room 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 reaction mixture was purified by flash chromatography (silica gel, 100% heptane to 100% ethyl acetate) to provide the title compound (3.15 g, 53% yield).

後処理

  1. additionafter complete addition
  2. concentrationThe mixture was concentrated under vacuum
  3. temperatureThe resulting mixture was heated to 75° C. for 2 hours
  4. temperaturethen cooled to room temperature
  5. customThe mixture was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe reaction mixture was purified by flash chromatography (silica gel, 100% heptane to 100% ethyl acetate)

出典と根拠

ORDレコード
ord-f7fb6e2e606b416c8e83f761f428c6e8
出典データセット
uspto-grants-2016_04
特許番号
US09321764B2

関連ノート

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