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

反応式

HRID 595668 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 903324215-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ade4085fa6194ffaae10b313b720147a
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

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