Methyl iodide → HCID 71295249, compound

HRID 1776906Notes

Reaction equation

HRID 1776906 reaction equation
[Br:1][C:2]1[C:3]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:7]([C:18]([NH:20][CH3:21])=[O:19])[C:6]=2[CH:22]=1.[C:28]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:3]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:25])=[O:26])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:7]([C:18]([NH:20][CH3:21])=[O:19])[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71294979HCID 71294979, compound

Product 1

HCID 71295249HCID 71295249, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-(2,4-difluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (653 mg, 1.38 mmol), K2CO3 (406 mg, 2.94 mmol) in DMF (10 mL) was added MeI (519 mg, 3.66 mmol), then the mixture was stirred at 80° C. After 3 hours, the solvent was removed by vacuum, the mixture was washed with H2O (20 mL) and extract with dichloromethane (50 mL*3), dried over Na2SO4 and concentrated to provide 5-bromo-2-(2,4-difluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (118 mg, yield: 25%). 1H-NMR (CDCl3, 400 MHz) 8.24 (s, 1H), 7.69˜7.75 (m, 2H), 7.05˜7.10 (m, 1H), 6.98˜7.03 (m, 1H), 5.64 (d, J=3.0 Hz, 1H), 3.09 (s, 3H), 2.97 (s, 3H), 2.95 (s, 3H). MS (M+H)+: 473/475.

Workup

  1. customthe solvent was removed by vacuum
  2. washthe mixture was washed with H2O (20 mL)
  3. extractionextract with dichloromethane (50 mL*3)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-576becf33b98478fbc364c977264488a
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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