Sodium hydride → 5-(2-fluoropyridin-3-yl)-1-(2-furylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 1426658노트

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HRID 1426658 반응식
[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[S:37](Cl)(=[O:39])=[O:38]>O1CCCC1.C(=O)([O-])O.[Na+]>[F:1][C:2]1[C:7]([C:8]2[N:12]([S:37]([C:33]3[O:32][CH:36]=[CH:35][CH:34]=3)(=[O:39])=[O:38])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2795072Furan-2-sulfonyl ChlorideHCID 58349828HCID 58349828, 화합물

생성물 1

HCID 866239765-(2-fluoropyridin-3-yl)-1-(2-furylsulfonyl)-1H-pyrrole-3-carbaldehyde수율 83%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (220 mg) in tetrahydrofuran (30 mL) was added sodium hydride (60% in oil, 84 mg) at room temperature and the mixture was stirred for 10 min. 15-Crown-5 (464 mg) was added dropwise, and the mixture was stirred for 5 min. Furan-2-sulfonyl chloride (263 mg) was added, and the mixture was further stirred for 30 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) and crystallized from diethyl ether to give the title compound as colorless crystals (yield 280 mg, 83%).

후처리

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was further stirred for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1)
  8. customcrystallized from diethyl ether

출처 및 근거

ORD 기록
ord-edc118d5cc464276a0a1b5c9e47714c5
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933105B2

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