Potassium Carbonate → 5-Cyclopropylmethoxy-1H-indol

HRID 41063

Reaktionsgleichung

Reaktionsgleichung von HRID 41063
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]1([CH2:12][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 81503Bromomethylcyclopropane2×

Produkt 1

HCID 574369835-Cyclopropylmethoxy-1H-indol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 7.3 g 5-hydroxy-indole in 130 ml of dry acetone are added 10.5 ml bromomethyl cyclopropane and 22.7 g anhydrous potassium carbonate. The mixture is heated to reflux for 24 h and an additional amount of 5 ml bromomethyl cyclopropane are added. The mixture is heated to reflux for additional 4 days. The mixture is filtered and the solvent is removed under reduced pressure. The residue is dissolved in dichloro methane and washed with an aqueous solution of hydrochloric acid (2 M), 10% aq. NaHCO3 and water. The organic layer is dried and the solvent is removed under reduced pressure. After purification by column chromatography (silica gel; toluene, acetone 95:5), 9.62 g, 94%) of the title compound are obtained as an oil. 1H-NMR (CDCl3): 0.36 (m, 2H, cyclopropyl CH2), 0.64 (m, 2H, cyclopropyl CH2), 1.30 (m, 1H, cyclopropyl CH), 3.83 (d, 2H, J=7.0 Hz, CH2O), 6.45 (s, 1H, aromatic), 6.90 (dd, 1H, aromatic), 7.09-7.27 (m, 3H, aromatic), 8.05 (bs, 1H, NH). 13C-NMR (CDCl3): 3.1 (2 cyclopropyl CH2), 10.4 (cyclopropyl CH), 74.2 (CH2O), 101.2, 101.6, 104.0, 104.6, 149.8 (aromatic)

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 h
  3. temperatureThe mixture is heated
  4. temperatureto reflux for additional 4 days
  5. filtrationThe mixture is filtered
  6. customthe solvent is removed under reduced pressure
  7. dissolutionThe residue is dissolved in dichloro methane
  8. washwashed with an aqueous solution of hydrochloric acid (2 M), 10% aq. NaHCO3 and water
  9. customThe organic layer is dried
  10. customthe solvent is removed under reduced pressure
  11. customAfter purification by column chromatography (silica gel; toluene, acetone 95:5), 9.62 g, 94%) of the title compound
  12. customare obtained as an oil

Quellen und Nachweise

ORD-Eintrag
ord-6920e4434f3d4db69bd1d676b22b48e8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530493B2

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