Iodine → 1-Iodoisoquinoline

HRID 1094669ノート

反応式

HRID 1094669 の反応式
[Li+].[Cl-].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[I:13]I>C1COCC1>[I:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

参加物

5

反応物 3

HCID 807IodineHCID 8405IsoquinolineHCID 433294Lithium Chloride

生成物 1

HCID 6409641-Iodoisoquinoline収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with TMPMgCl LiCl (5 mL, 1.2 M in THF, 6.0 mmol). Isoquinoline (703 mg, 5.45 mmol) in THF (5 ml) was added dropwise at room temperature. During addition, the reaction mixture became red and the metalation was complete after 2 h (as checked by GC analysis of reaction aliquots quenched with a solution of I2 in THF, the conversion was more than 98%). A solution of I2 in THF (6 ml, 1 M in THF, 6.0 mmol) was slowly added at −20° C. The reaction mixture was quenched with sat. aqueous NH4Cl solution (10 mL). The aqueous phase was extracted with ether (4×10 mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by filter column chromatography (CH2Cl2/pentane) yielding 1-iodoisoquinoline (7a; 1.33 mg, 96%) as slightly yellow crystals (mp=74-76° C.).

後処理

  1. customA dry
  2. customargon flushed 10 mL flask
  3. customequipped with a magnetic stirrer
  4. additionDuring addition
  5. custom(as checked by GC analysis of reaction aliquots
  6. customquenched with a solution of I2 in THF
  7. customThe reaction mixture was quenched with sat. aqueous NH4Cl solution (10 mL)
  8. extractionThe aqueous phase was extracted with ether (4×10 mL)
  9. dry with materialdried with Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was purified
  12. filtrationby filter column chromatography (CH2Cl2/pentane)

出典と根拠

ORDレコード
ord-50bb78ed6cf54a958d331611bafdf386
出典データセット
uspto-grants-2012_03
特許番号
US08134005B2

反応ノート

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