Hydrogen Bromide → Methyl3-Formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

HRID 40098

Reaktionsgleichung

Reaktionsgleichung von HRID 40098
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Br.[OH-].[Na+].[CH3:12][O:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([C:24]=1[CH:25]=[O:26])=[CH:22][CH:21]=[C:20]([O:27][CH3:28])[CH:19]=2)=[O:15].C([O-])([O-])=O.[K+].[K+]>CCOCC.CN(C=O)C>[CH:25]([C:24]1[C:23]2[C:18](=[CH:19][C:20]([O:27][CH3:28])=[CH:21][CH:22]=2)[N:17]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[C:16]=1[C:14]([O:13][CH3:12])=[O:15])=[O:26]

Komponenten

8

Edukt 5

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5642092-(Bromomethyl)pyridineHCID 4777855Methyl 3-formyl-6-methoxy-1H-indole-2-carboxylate2×

Produkt 1

HCID 59762382Methyl3-Formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

General Procedure J. 2-Bromomethylpyridine.HBr salt (7.0 g, 27.7 mmol) was treated with NaOH (4M, 6.9 ml, 27.6 mmol) in Et2O (20 ml). The ether layer was separated, washed with brine, and dried over MgSO4, filtered into a flask containing a suspension of methyl3-formyl-6-methoxy-1H-indole-2-carboxylate (Compound 90, 1.29 g, 5.54 mmol) and K2CO3 (2.3 g, 16.6 mmol) in DMF (25 ml). The reaction was stirred at 60° C. for 3 h, cooled to room temperature, quenched with H2O and extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by washing with H2O (×3) and filtration to yield the title compound as a golden brown solid.

Aufarbeitung

  1. customThe ether layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered into a flask
  5. additioncontaining
  6. temperaturecooled to room temperature
  7. customquenched with H2O
  8. extractionextracted with EtOAc (×2)
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified
  13. washby washing with H2O (×3) and filtration

Quellen und Nachweise

ORD-Eintrag
ord-eb22265ff8ae48ce943d2a17ad525da2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

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