Ammonium Chloride → 1-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-ol

HRID 1506229ノート

反応式

HRID 1506229 の反応式
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12.[CH2:21]([Mg]Br)[CH3:22].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:21][CH3:22])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 866767394-Chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeHCID 178420660HCID 178420660、化合物

生成物 1

HCID 712584341-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-ol収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (117 mg, 0.360 mmol) in tetrahydrofuran (2 mL) was mixed with ethylmagnesium bromide-tetrahydrofuran solution (1.0 M, 1.0 mL, 1.0 mmol) under cooling with ice and stirred at room temperature for one day. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 (v/v)) to give the title compound as a colorless oil (75.6 mg, yield 62%).

後処理

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 (v/v))

出典と根拠

ORDレコード
ord-87b1af9629c24331b30b28c0d9f2fabc
出典データセット
uspto-grants-2015_12
特許番号
US09216999B2

反応ノート

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