Ethylamine → 3-bromo-6-ethyl-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one

HRID 1778739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778739
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12]Br)[C:5]([C:8]([O:10]C)=O)=[N:6][CH:7]=1.[CH2:14]([NH2:16])[CH3:15].C1COCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][N:16]([CH2:14][CH3:15])[C:8](=[O:10])[C:5]2=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 58171990Methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylate

Produkt 1

HCID 867228403-bromo-6-ethyl-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of methyl 5-bromo-3-(bromomethyl)pyridine-2-carboxylate (0.39 g, 1.3 mmol), ethylamine in THF (0.88 mL, 2.0 M, 1.8 mmol) and potassium carbonate (0.26 g, 1.9 mmol) in ethanol (5 mL) in a sealed reaction vial was stirred at 40° C. for 2 h. The solid was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.24 g). LCMS (M+H)+=240.9/242.9.

Aufarbeitung

  1. customin a sealed reaction vial
  2. filtrationThe solid was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-4c6286026f894681b4675b8fbb821782
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266892B2

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