Ethyl 1-propenyl ether → 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595668

Reaktionsgleichung

Reaktionsgleichung von HRID 595668
[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10](Cl)=[N:11][OH:12])=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[C:6]=2[CH:18]=1.[CH2:25]([O:27][CH:28]=[CH:29][CH3:30])[CH3:26].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:29]([CH3:30])[CH:28]([O:27][CH2:25][CH3:26])[O:12][N:11]=3)=[C:7]([C:14]([NH:15][CH3:16])=[O:17])[C:6]=2[CH:18]=1

Komponenten

5

Edukt 3

HCID 13570Ethyl 1-propenyl etherHCID 516892Sodium BicarbonateHCID 903324475-bromo-N-hydroxy-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carbimidoyl chloride

Produkt 1

HCID 903324215-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-N-hydroxy-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carbimidoyl chloride (400 mg, 0.91 mmol), 1-ethoxyprop-1-ene (392 mg, 4.56 mmol) and NaHCO3 (153 mg, 1.82 mmol) in DMF (10 mL) was stirred at room temperature for 16 h. It was concentrated, diluted with water, extracted with EtOAc, the organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (PE:EA=2:1) to get product 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (370 mg, yield: 83%). MS (M+H)+: 488/490.

Aufarbeitung

  1. concentrationIt was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washthe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (PE:EA=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ade4085fa6194ffaae10b313b720147a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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