Sodium hydride → 1-[(2-fluorophenyl)sulfonyl]-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

HRID 1426657노트

반응식

HRID 1426657 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.[F:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39](Cl)(=[O:41])=[O:40]>O1CCCC1.[Cl-].[Na+].O>[F:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39]([N:12]1[C:8]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][C:10]([CH:13]=[O:14])=[CH:11]1)(=[O:41])=[O:40]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 58349828HCID 58349828, 화합물

생성물 1

HCID 866239751-[(2-fluorophenyl)sulfonyl]-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde수율 82%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (80 mg) in tetrahydrofuran (8 mL) was added sodium hydride (60% in oil, 34 mg) at room temperature, and the mixture was stirred for 10 min. 15-Crown-5 (186 mg) was added dropwise, and the mixture was stirred for 5 min. 2-Fluorobenzenesulfonyl chloride (123 mg) was added, and the mixture was further stirred for 1 hr. The reaction mixture was diluted with saturated brine, 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=4:1→1:1) to give the title compound as a colorless oil (yield 120 mg, 82%).

후처리

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was further stirred for 1 hr
  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=4:1→1:1)

출처 및 근거

ORD 기록
ord-8a5cadc331fc4441b47d1112d1a40720
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933105B2

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