N,N'-Dimethylethylenediamine → HCID 59375096, Verbindung

HRID 1811011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811011
[F:1][C:2]1[C:3](I)=[N:4][CH:5]=[CH:6][C:7]=1[I:8].[C:10]1(=[O:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[F:1][C:2]1[C:3]([N:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]2=[O:19])=[N:4][CH:5]=[CH:6][C:7]=1[I:8]

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 10199PhthalimidineHCID 11430Potassium CarbonateHCID 99979273-Fluoro-2,4-diiodopyridine

Produkt 1

HCID 59375096HCID 59375096, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 3-fluoro-2,4-diiodopyridine (300 mg, 0.860 mmol), isoindolin-1-one (114 mg, 0.860 mmol), copper (I) iodide (8.19 mg, 0.043 mmol), potassium carbonate (238 mg, 1.720 mmol) and N1,N2-dimethylethane-1,2-diamine (7.58 mg, 0.086 mmol) in 1,4-dioxane (5 mL) was heated at 110° C. in a sealed tube for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one (125 mg, 41%). 1H NMR (400 MHz, chloroform-d) δ 7.86-8.06 (2 H, m), 7.41-7.71 (4 H, m), 5.04 (2 H, s). Mass spectrum m/z 354.9 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (
  6. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-acf015592d0143889f12118095992fe2
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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