Cesium carbonate → (S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylate

HRID 1184411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184411
Br[C:2]1[N:3]=[CH:4][C:5]([C:15]([O:17][CH3:18])=[O:16])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]([F:31])([F:30])[C@@H:27]([OH:29])[CH3:28]>CS(C)=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[N:6]=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[N:3][C:2]=2[O:29][C@@H:27]([CH3:28])[C:26]([F:31])([F:30])[F:25])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 6999971(2S)-1,1,1-Trifluoropropan-2-olHCID 86619571Methyl 5-bromo-6-(4-chlorophenyl)pyrazine-2-carboxylate

Produkt 1

HCID 66678867(S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylateAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-bromo-6-(4-chlorophenyl)pyrazine-2-carboxylate (0.847 g, 2.59 mmol, Eq: 1.00) in dry DMSO (8 ml) was added cesium carbonate (1.54 g, 2.84 mmol, Eq: 1.1) and (S)-1,1,1-trifluoro-2-propanol (324 mg, 233 μl, 2.84 mmol, Eq: 1.1) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was dried over MgSO4 evaporated and purified by flash chromatography (silica gel, 100 g, 10% to 50% ethyl acetate in heptane) to yield the title compound as light yellow oil (0.724 g, 77.6%). MS (EI): 361.1 (M+H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases were separated
  3. dry with materialthe organic phase was dried over MgSO4
  4. customevaporated
  5. custompurified by flash chromatography (silica gel, 100 g, 10% to 50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-981bb6d9a53d429b8ef03f5a4dccb3e7
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669254B2

Notizen zur Reaktion

Wird geladen…