Methyl iodide → HCID 90332417, compound

HRID 595594Notes

Reaction equation

HRID 595594 reaction equation
[Br:1][C:2]1[C:3]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:12][CH2:11]3)=[C:7]([C:13]([NH:15][CH3:16])=[O:14])[C:6]=2[CH:17]=1.[C:23]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:3]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:20])=[O:21])=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:11][CH2:12]3)=[C:7]([C:13]([NH:15][CH3:16])=[O:14])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 90332963HCID 90332963, compound

Product 1

HCID 90332417HCID 90332417, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of compound 5-bromo-2-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (1.5 g, 3.9 mmol) and K2CO3 (1.6 mg, 7.8 mmol) in DMF (15 mL) was added dropwise CH3I (1.1 mg, 7.8 mmol) at 0° C. under N2, and then the mixture was stirred at 80° C. for 2 hours. After concentration in vacuum, the residue was suspended in H2O and extracted with DCM. The combined organic layer was washed with H2O, brine and dried over Na2SO4. The mixture was filtered and concentrated to give the product of compound 5-bromo-2-cyclopropyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1 g, yield: 65%). 1H-NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 6.98 (s, 1H), 5.63 (s, 1H), 3.05 (s, 3H), 2.79 (s, 6H), 2.39˜2.43 (m, 1H), 0.95˜0.97 (m, 2H), 0.89˜0.91 (m, 2H). MS (M+H)+: 401/403.

Workup

  1. concentrationAfter concentration in vacuum
  2. extractionextracted with DCM
  3. washThe combined organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6155f0d87d5340cabf4bd34016bfab53
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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