N,N'-Dimethylethylenediamine → 2-(5-Bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one

HRID 661828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661828
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8].C[C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][NH:16][C:17]2=[O:20])=[CH:13][CH:12]=1.[C:21](=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Br:9][C:6]1[C:7]([CH3:8])=[C:2]([N:16]2[CH2:15][C:14]3[C:18](=[CH:19][CH:11]=[C:12]([CH3:21])[CH:13]=3)[C:17]2=[O:20])[CH:3]=[N:4][CH:5]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 8193383,5-Dibromo-4-methylpyridineHCID 124964736-Methyl-2,3-dihydro-1H-isoindol-1-one

Produkt 1

HCID 593751432-(5-Bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-oneAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Step 2 A mixture of 3,5-dibromo-4-methylpyridine (2.00 g, 7.97 mmol), 6-methylisoindolin-1-one (1.173 g, 7.97 mmol), copper (I) iodide (0.076 g, 0.399 mmol), potassium carbonate (2.203 g, 15.94 mmol) and N1,N2-dimethylethane-1,2-diamine (0.070 g, 0.797 mmol) in 1,4-dioxane (20 mL) was heated at 100° C. for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was diluted with DCM (100 mL) and washed with water (10 mL) and brine (10 mL), then was dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one (760 mg, 30%). 1H NMR (400 MHz, chloroform-d) δ 8.68 (1H, s), 8.42 (1H, s), 7.84 (1H, d, J=7.77 Hz), 7.37 (1H, d, J=7.77 Hz), 7.34 (1H, s), 4.73 (2H, s), 2.50 (3H, s), 2.35 (3H, s). Mass spectrum m/z 317, 319 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. washwashed with DCM
  4. additionThe filtrate was diluted with DCM (100 mL)
  5. washwashed with water (10 mL) and brine (10 mL)
  6. customwas dried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (
  9. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a2c4ad030fb54265af157e0a01be2f39
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084620B2

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