Diiodomethane → 3-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile

HRID 56237

Reaktionsgleichung

Reaktionsgleichung von HRID 56237
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20].I[CH2:25]I>CN(C=O)C>[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][N:12]2[CH2:25][O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[C:19]#[N:20])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Komponenten

6

Edukt 4

HCID 6346DiiodomethaneHCID 133943-CyanophenolHCID 24758Sodium hydrideHCID 785026-Nitro-1H-indole

Produkt 1

HCID 900304473-((6-nitro-1H-indol-1-yl)methoxy)benzonitrileAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel4×

Versuchsvorschrift

To a mixture of NaH (3.0 g, 75.0 mmol, 60%) in DMF (20 mL) were added a solution of 6-nitro-1H-indole (4.86 g, 30.0 mmol) in DMF (10 mL) and a solution of 3-hydroxybenzonitrile (3.57 g, 30.0 mmol) in DMF (10 mL) at 0° C. and the mixture was stirred at rt for 2 h. To the reaction mixture was added a solution of diiodomethane (7.5 mL, 90.0 mmol) in DMF (10 mL) slowly without light and the mixture was stirred at rt for 20 h. The mixture was then quenched with water and filtered. The filtrate was extracted with DCM (30 mL×6) and the combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (4.47 g, 51%).

Aufarbeitung

  1. customThe mixture was then quenched with water
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with DCM (30 mL×6)
  4. washthe combined organic layers were washed with brine (50 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4ac7af751afe4a0c8814018ded4486d1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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