Cesium carbonate → HCID 11197250, Verbindung

HRID 2240906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240906
[F:1][C:2]([F:16])([F:15])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([C:13]#[N:14])[C:8]([C:11]#[N:12])=[CH:9][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CC#N>[C:13]([C:7]1[CH:6]=[C:5]([N:4]([CH2:3][C:2]([F:15])([F:16])[F:1])[CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:10]=[CH:9][C:8]=1[C:11]#[N:12])#[N:14]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 576337284-[(2,2,2-Trifluoroethyl)amino]-1,2-benzenedicarbonitrile

Produkt 1

HCID 11197250HCID 11197250, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 4-[(2,2,2-trifluoroethyl)amino]-1,2-benzenedicarbonitrile (0.020 g, 0.089 mmol) in MeCN (3 mL) was treated with Cs2CO3 (0.078 g, 0.24 mmol) and methyl bromoacetate (0.037 g, 0.24 mmol) and heated at 85° C. under nitrogen for 8 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (20-100% CH2Cl2-hexanes gradient) and the product crystallized from CH2Cl2-hexanes to give 0.015 g (58% yield) of the title compound as a white solid: MS (ES) m/z 296 (M−1).

Aufarbeitung

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (20-100% CH2Cl2-hexanes gradient)
  7. customthe product crystallized from CH2Cl2-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-df18a62da7804610ba0b5c91541ba94e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723385B2

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