Imidazole → 3-(((Tert-butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridine

HRID 2401380ノート

反応式

HRID 2401380 の反応式
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([I:10])[CH:5]=[CH:4][N:3]=1.N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(OCC)C>C(Cl)Cl>[Si:20]([O:9][CH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][C:6]=1[I:10])([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 11021396(2-Fluoro-4-iodopyridin-3-yl)methanol

生成物 1

HCID 678131863-(((Tert-butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridine収率 88.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2-fluoro-4-iodopyridin-3-yl)methanol (3.52 g, 13.91 mmol) in CH2Cl2 (80 mL) at room temperature was sequentially added imidazole (1.894 g, 27.8 mmol) and TBDMS-Cl (2.52 g, 16.69 mmol). The reaction was stirred at room temperature for 1 h before diethylether was added and the insoluble salts were filtered. Silica gel was added to the filtrate prior to the solvent removal under vacuum. The dry silica gel was packed, and the adsorbed product was purified by flash chromatography (hexane/EtOAc 10:0 to 7:3) to give 3-(((tert-butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridine as a white solid (4.5 g). LC/MS m/z 368 [M+H]+.

後処理

  1. customat room temperature
  2. additionwas added
  3. filtrationthe insoluble salts were filtered
  4. additionSilica gel was added to the filtrate
  5. customto the solvent removal under vacuum
  6. customthe adsorbed product was purified by flash chromatography (hexane/EtOAc 10:0 to 7:3)

出典と根拠

ORDレコード
ord-b7cb33db9990474f802c0732ab24d1b9
出典データセット
uspto-grants-2014_08
特許番号
US08796261B2

反応ノート

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