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

HRID 633553

반응식

HRID 633553 반응식
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

참가 물질

7

반응물 4

HCID 6340IodoethaneHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate2회HCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

생성물 1

HCID 593265653-Bromo-2-chloro-5-(ethylsulfonyl)pyridine수율 53.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f7fb6e2e606b416c8e83f761f428c6e8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321764B2

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