Methyl iodide → HCID 68815178, Verbindung

HRID 732463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732463
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:5]=1.IC.[C:23](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([N:15]([S:16]([CH3:19])(=[O:18])=[O:17])[CH3:23])[CH:5]=1

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68814746HCID 68814746, Verbindung

Produkt 1

HCID 68815178HCID 68815178, VerbindungAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolve 2-methanesulfonylamino-6-(methylpropylamino)-isonicotinic acid methyl ester (87 mg, 2.89 mmol) and iodomethane (0.27 mL, 4.33 mmoles) in DMF (10 mL). Add potassium carbonate (639 mg, 4.62 mmol) and tetrabutylammonium bromide (93 mg, 0.98 mmol) and stir at room temperature 1 h. Dilute with ethyl acetate (80 mL), wash with 10% aqueous potassium carbonate (2×15 mL), 0.1 N citric acid (2×15 mL), 1 N lithium chloride (2×15 mL) and saturated aqueous sodium chloride (15 mL). Concentrate organic layer and purify (silica gel chromatography, eluting with 10:90 to 40:60 ethyl acetate:hexanes to give the title compound (796 mg, 87%).

Aufarbeitung

  1. washwash with 10% aqueous potassium carbonate (2×15 mL), 0.1 N citric acid (2×15 mL), 1 N lithium chloride (2×15 mL) and saturated aqueous sodium chloride (15 mL)
  2. customConcentrate organic layer and purify (silica gel chromatography
  3. washeluting with 10:90 to 40:60 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bc8171f004c74e3390b07f6599b24477
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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