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

HRID 1426657ノート

反応式

HRID 1426657 の反応式
[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]

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 58349828HCID 58349828、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8a5cadc331fc4441b47d1112d1a40720
出典データセット
uspto-grants-2015_01
特許番号
US08933105B2

反応ノート

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