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

HRID 595604노트

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HRID 595604 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b240ea58c2a2442190108c6bf19a0542
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242998B2

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