Triisopropylsilyl chloride → HCID 57830996、化合物

HRID 1642070ノート

反応式

HRID 1642070 の反応式
[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1

参加物

5

反応物 2

HCID 139400Triisopropylsilyl chlorideHCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

生成物 1

HCID 57830996HCID 57830996、化合物収率 95%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A solution of the 2-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine from the previous step in 30 mL of tetrahydrofuran stirring at 0° C. under argon atmosphere was treated with lithium hexamethyldisilylazide (6 mL, 1 M in hexanes, 6 mmol), followed by triisopropylsilyl chloride (1.1 mL, 5.2 mmol). After 30 m at 0° C., the solution was warmed to ambient temperature and diluted with 20% ethyl acetate in hexanes, then washed twice with water and once with brine. After drying the organic layer over magnesium sulfate, filtration was followed by solvent removal and flash chromatography of the resultant residue using 2.5% ethyl acetate in hexanes, to furnish 2-Chloro-7-iodo-5-triisopropylsilanyl-5H-pyrrolo[2,3-b]pyrazine (1.68 g, 95% over two steps).

後処理

  1. washwashed twice with water and once with brine
  2. customAfter drying the organic layer
  3. filtrationover magnesium sulfate, filtration
  4. customwas followed by solvent removal and flash chromatography of the resultant residue

出典と根拠

ORDレコード
ord-4bb39287e5954cb5ba01a03605858fe1
出典データセット
uspto-grants-2012_02
特許番号
US08119636B2

反応ノート

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