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Sodium hydride → tert-butyl({5-bromo-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate

HRID 1012518
ノート
印刷プレビュー

反応式

HRID 1012518 の反応式
[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([Br:15])[NH:12][CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:34][C:35]1[N:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>O1CCCC1.O>[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([Br:15])[N:12]([S:41]([C:38]2[CH:39]=[N:40][C:35]([CH3:34])=[CH:36][CH:37]=2)(=[O:43])=[O:42])[CH:11]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 223987146-Methylpyridine-3-sulfonyl chlorideHCID 57522147tert-Butyl ((5-bromo-1H-pyrrol-3-yl)methyl)(methyl)carbamate

生成物 1

HCID 66974470tert-butyl({5-bromo-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate収率 79%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of tert-butyl[(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (207 mg) in tetrahydrofuran (30 mL) was added sodium hydride (60% in oil, 31 mg) at 0° C., and the mixture was stirred at the same temperature for 10 min. A solution (3 mL) of 15-crown-5 (0.16 mL) and 6-methylpyridin-3-ylsulfonyl chloride (117 mg) in tetrahydrofuran was added at the same temperature. After stirring at room temperature for 30 min, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1) to give the title compound as a brown oil (yield 213 mg, 79%).

後処理

  1. stirringAfter stirring at room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-1cd83f3f5dbd4c9a8c373c2dc31ea413
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977488B2

反応ノート

読み込み中…

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