Water → 1H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 1-[tris(1-methylethyl)silyl]-

HRID 253367

反応式

HRID 253367 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15].O>O1CCCC1>[CH:14]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1)([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

生成物 1

HCID 497589651H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 1-[tris(1-methylethyl)silyl]-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (7, 4.05 g, 27.71 mmol) in tetrahydrofuran (30.0 mL) were added sodium hydride (60% in mineral oil, 1.5 g, 38 mmol) and triisopropylsilyl chloride (8.0 mL, 38 mmol) under an atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 10% ethyl acetate in hexane to give the compound (8, 3.0 g, 36%). MS (ESI) [M+H+]+=303.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 10% ethyl acetate in hexane
  8. customto give the compound (8, 3.0 g, 36%)

出典と根拠

ORDレコード
ord-ff80739cdbc2437b9b4f832d81473d38
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

関連ノート

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