Methyl iodide → (1-Methyl-1H-indol-6-yl)boronic acid

HRID 1878907

Reaktionsgleichung

Reaktionsgleichung von HRID 1878907
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:10]([OH:12])[OH:11])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:15]1COCC1.CI>>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([B:10]([OH:12])[OH:11])[CH:8]=2)[CH:3]=[CH:2]1

Komponenten

5

Edukt 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27632051H-Indol-6-ylboronic acid

Produkt 1

HCID 21709054(1-Methyl-1H-indol-6-yl)boronic acid

Versuchsvorschrift

A mixture of indole-6-boronic acid (0.100 g, 0.615 mol), sodium hydride (0.07 g, 20 mmol) and THF (5 mL, 60 mmol) was stirred at rt for 20 min. then methyl iodide (100 uL, 20 mmol) was added and the mixture was allowed to stir at rt for 3 hours. The reaction was quenched with sat. NH4Cl solution, washed with brine and dried over Na2SO4, then the solvent was removed in vacuo. The crude product was purified by chromatography over silica gel eluting with 1:9 EtOAc/hexane and 1% MeOH, yielding the desired product. 1H NMR (400 MHz, CDCl3) δ ppm 3.99 (s, 3H), 6.58 (m, 1H). 7.23 (m, 1H), 7.81 (m, 1H), 8.08 (m, 1H) and 8.34 (m, 1H). MS (ES+): m/z 176.15 [MH+].

Aufarbeitung

  1. stirringto stir at rt for 3 hours
  2. customThe reaction was quenched with sat. NH4Cl solution
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by chromatography over silica gel eluting with 1:9 EtOAc/hexane and 1% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-3add17858fa34c3bb2c35263d8ed6d53
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314111B2

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