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

HRID 595575
Notes
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Reaction equation

HRID 595575 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b29beab373f94097b2c27b8b9077f478
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242998B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes