Water → 5-bromo-2-iodo-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

HRID 595640Notes

Reaction equation

HRID 595640 reaction equation
[NH2:1][C:2]1[C:15]([Br:16])=[CH:14][C:5]2[C:6]([C:10]([NH:12][CH3:13])=[O:11])=[C:7]([I:9])[O:8][C:4]=2[CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O.O[Li].O>N1C=CC=CC=1>[Br:16][C:15]1[C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:3][C:4]2[O:8][C:7]([I:9])=[C:6]([C:10]([NH:12][CH3:13])=[O:11])[C:5]=2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 903324376-amino-5-bromo-2-iodo-N-methylbenzofuran-3-carboxamide

Product 1

HCID 903323955-bromo-2-iodo-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamideYield 66.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-amino-5-bromo-2-iodo-N-methylbenzofuran-3-carboxamide (1 g, 2.53 mmol) in pyridine, MsCl (580 mg, 5.06 mmol) was added dropwise at 0° C. The mixture was allowed to warm to room temperature and stirred for 1.5 h. After the solvent was removed in vacuo, the reaction mixture was adjusted to pH=5-6 with 1 N HCl aq. After filtration, the solid was dissolved in THF:H2O=5:1 (15 mL) and then LiOH.H2O (800 mg, 20 mmol) was added. The mixture was stirred for 30 minutes at room temperature. After the solvent was removed in vacuo, the reaction mixture was adjusted to pH=5-6 with 1 N HCl aq. Finally the precipitate was collected to give 5-bromo-2-iodo-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (800 mg, 90% purity by HPLC, yield: 60%), which was used for the next step without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.37 (s, 1H), 7.84 (s, 1H), 6.86 (s, 1H), 6.29 (s, 1H), 3.07 (d, J=4.8 Hz, 3H), 2.99 (s, 3H). MS (M+H)+: 473/475.

Workup

  1. customAfter the solvent was removed in vacuo
  2. filtrationAfter filtration
  3. dissolutionthe solid was dissolved in THF
  4. stirringThe mixture was stirred for 30 minutes at room temperature
  5. customAfter the solvent was removed in vacuo
  6. customwas collected

Sources & evidence

ORD record
ord-ebb8a0e766c041fcae6e710260a92dc3
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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