Carbon Dioxide → 5-iodo-1-methyl-1H-indole

HRID 984491

反応式

HRID 984491 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].IC.[C:15](=O)=O>C1COCC1.CCCCCC.CCOCC>[CH3:15][N:7]1[C:8]2[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27823135-Iodo-1H-indole

生成物 1

HCID 113228355-iodo-1-methyl-1H-indole

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a solution of 5-iodoindole (75 g, 0.31 mol) in dry THF (750 mL), at −78° C. was added sodium hydride (60% in mineral oil, 14.85 g, 0.37 mol) in one portion. The suspension was stirred at −78° C. for 1 hour after which iodomethane (28.8 mL, 0.46 mol) was added. The reaction mixture was stirred overnight with a slow elevation of temperature to room temperature (no more dry ice was added). Ether (600 mL) and hexane (1.2 L) were added and the mixture was washed with brine (1.6 L) and water (1.5 L), dried over Na2SO4 and filtered. The solution was concentrated and the residual brown solid was recrystallized from hexane to give the title compound (66 g). The impure fraction from the mother liquor was flash chromatographed (8% EtOAc in hexane) to give an additional quantity of desired product (12.5 g, combined yield of 99%). MS (DCI/NH3) m/e 258 (M+H)+.

後処理

  1. additionwas added
  2. additionwas added)
  3. washthe mixture was washed with brine (1.6 L) and water (1.5 L)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe solution was concentrated
  7. customthe residual brown solid was recrystallized from hexane

出典と根拠

ORDレコード
ord-5ed9a02dfa824f8b99de2715a2e404ae
出典データセット
uspto-grants-2005_03
特許番号
US06867203B2

関連ノート

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