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Imidazole → 5-bromo-2-(1H-imidazol-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595575
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HRID 595575 반응식
[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.C([O-])([O-])=O.[K+].[K+].[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1>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:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1
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5

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HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 903324695-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 903335425-bromo-2-(1H-imidazol-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a degassed solution of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.21 mmol) and K2CO3 (43 mg, 0.31 mmol) in DMF (1 mL) was added 1H-imidazole (14 mg, 0.21 mmol) under N2 at 0° C. The mixture was heated at 60° C. for 10 hours. The reaction mixture was concentrated and it was extracted with EtOAc. The residue was washed with H2O, brine, dried over Na2SO4. After being concentrated, the crude product was purified by column (PE:EA=1:1) to give of 5-bromo-2-(1H-imidazol-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (72 mg, yield: 83%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.40 (d, J=4.4 Hz, 1H), 8.36 (s, 1H), 8.10 (s, 2H), 7.80 (s, 1H), 7.19 (s, 1H), 3.21 (s, 3H), 3.20 (s, 3H), 2.81 (d, J=4.4 Hz, 3H). MS (M+H)+: 427/429.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. extractionit was extracted with EtOAc
  3. washThe residue was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter being concentrated
  6. customthe crude product was purified by column (PE:EA=1:1)

출처 및 근거

ORD 기록
ord-b29beab373f94097b2c27b8b9077f478
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242998B2

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