Methyl iodide → 2-acetyl-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595604ノート

反応式

HRID 595604 の反応式
[C:1]([C:4]1[O:5][C:6]2[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:14]([Br:22])=[CH:13][C:7]=2[C:8]=1[C:9]([NH:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[C:23]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[C:1]([C:4]1[O:5][C:6]2[CH:16]=[C:15]([N:17]([CH3:23])[S:18]([CH3:21])(=[O:19])=[O:20])[C:14]([Br:22])=[CH:13][C:7]=2[C:8]=1[C:9]([NH:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 903324982-acetyl-5-bromo-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

生成物 1

HCID 903325622-acetyl-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide収率 45.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-acetyl-5-bromo-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (150 mg, 0.38 mmol) in DMF (3 mL) was added K2CO3 (160 mg, 1.16 mmol) and MeI (164 mg, 1.16 mmol). The mixture was heated at 60° C. for 1 hour, concentrated in vacuo to remove DMF and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product. The crude product was purified by column chromatography to give 2-acetyl-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (70 mg, yield: 45%). 1H-NMR (CDCl3, 400 MHz) δ 9.73 (s, 1H), 9.01 (s, 1H), 7.78 (s, 1H), 3.35 (s, 3H), 3.09 (s, 3H), 3.02 (d, J=4.8 Hz, 3H), 2.77 (s, 3H). MS (M+H)+: 403/405.

後処理

  1. concentrationconcentrated in vacuo
  2. customto remove DMF
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give crude product
  8. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-b240ea58c2a2442190108c6bf19a0542
出典データセット
uspto-grants-2016_01
特許番号
US09242998B2

反応ノート

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