Cesium carbonate → 4-chloro-2-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715208
Br[CH2:2][C:3]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7]CC)=O.Cl.[F:16][C:17]([F:30])([F:29])[CH2:18][O:19][C:20]1[N:25]=[CH:24][C:23]([CH:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Cl:14][C:13]1[C:3]2[CH2:2][N:28]([CH:26]([C:23]3[CH:24]=[N:25][C:20]([O:19][CH2:18][C:17]([F:30])([F:16])[F:29])=[CH:21][CH:22]=3)[CH3:27])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 675094131-[6-(2,2,2-Trifluoroethoxy)-pyridin-3-yl]-ethylamine hydrochlorideHCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinate

Produkt 1

HCID 898745024-chloro-2-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture (suspension) of ethyl 3-(bromomethyl)-2-chloroisonicotinate (698 mg, 2.5 mmol, Step-1), 1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (643 mg, 2.5 mmol, Amine-1, single enantiomer) and cesium carbonate (3.3 g, 10.0 mmol) in THF (20 mL) is heated at refluxed temperature overnight. After cooling to rt, the reaction mixture is filtered through a pad of Celite™, and washed with EtOAc. The filtrate is concentrated to give a brown suspension. The residue is purified by column chromatography on NH-gel eluting with n-hexane/EtOAc (4:1) to give 300 mg (32% yield) of the title compound as clear brown oil.

Aufarbeitung

  1. temperatureat refluxed temperature overnight
  2. filtrationthe reaction mixture is filtered through a pad of Celite™
  3. washwashed with EtOAc
  4. concentrationThe filtrate is concentrated
  5. customto give a brown suspension
  6. customThe residue is purified by column chromatography on NH-gel
  7. washeluting with n-hexane/EtOAc (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-37cad76c834c4cde949ee2fcda85d2ba
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187475B2

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