Potassium Carbonate → 5-bromo-N-methyl-2-(4-methyl-2-oxopyridin-1(2H)-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595661
[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8](I)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1.[CH3:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([OH:29])[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8]([N:26]3[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][C:25]3=[O:29])=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 903324695-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideHCID 178428601HCID 178428601, Verbindung

Produkt 1

HCID 903330925-bromo-N-methyl-2-(4-methyl-2-oxopyridin-1(2H)-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (500 mg, 1.03 mmol), 4-methylpyridin-2-ol (168 mg, 1.54 mmol) and K2CO3 (283 mg, 2.05 mmol) in DMF (5 mL) was stirred at 80° C. for 10 hours and concentrated in vacuo to remove DMF. The reaction mixture was extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (PE:EtOAc=1:1) to give the product of 5-bromo-N-methyl-2-(4-methyl-2-oxopyridin-1 (2H)-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (400 mg, yield: 83%). 1H-NMR (CDCl3, 400 MHz) δ 8.32 (s, 1H), 7.85 (s, 1H), 7.67 (s, 1H), 7.22 (d, J=7.2 Hz, 1H), 6.52 (s, 1H), 6.28 (d, J=1.6 Hz, 1H), 3.32 (s, 3H), 3.06 (s, 3H), 2.89 (d, J=4.8 Hz, 3H), 2.31 (s, 3H). MS (M+H)+: 468/470.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto remove DMF
  3. extractionThe reaction mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (PE:EtOAc=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c140e2d702424fe896a42020c019e8e5
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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