Dimethyl Sulfoxide → HCID 58466470, Verbindung

HRID 1668970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668970
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O.C(OCC)(=O)C>[I:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:17]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 73763-(Trifluoromethyl)phenolHCID 10796Cesium carbonateHCID 58466468HCID 58466468, Verbindung

Produkt 1

HCID 58466470HCID 58466470, VerbindungAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

1-Chloro-5-iodo-6-methylisoquinoline (0.250 g, 0.824 mmol), 3-(trifluoromethyl)phenol (0.200 g, 1.24 mmol), cesium carbonate (0.590 g, 1.81 mmol) were all placed in a clear microwave vial along with 3 ml of DMSO. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 170° C. for 20 minutes. The reaction was diluted with water and ethyl acetate. The organic layer washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 60-100% EtOAc in hexanes to give 5-iodo-6-methyl-1-(3-(trifluoromethyl)phenoxy)isoquinoline (0.260 g, 73.6% yield) as a white solid. MS (M+H)+ 430.

Aufarbeitung

  1. customThe vial was capped
  2. washThe organic layer washed (2×) with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. custompurified by column chromatography on silica gel using a gradient of 60-100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-501f829637204a0a9b2fb9d23f6c3c68
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989461B2

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