Methanesulfonyl chloride → 5-bromo-2-(4-cyanophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

HRID 595570Notes

Reaction equation

HRID 595570 reaction equation
[NH2:1][C:2]1[C:22]([Br:23])=[CH:21][C:5]2[C:6]([C:17]([NH:19][CH3:20])=[O:18])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl.N1C=CC=CC=1>[Br:23][C:22]1[C:2]([NH:1][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:3][C:4]2[O:8][C:7]([C:9]3[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[CH:13][CH:14]=3)=[C:6]([C:17]([NH:19][CH3:20])=[O:18])[C:5]=2[CH:21]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 903324446-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide

Product 1

HCID 903324155-bromo-2-(4-cyanophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamideYield 72.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide (300 mg, 0.80 mmol) in DCM (2 mL) and pyridine (2 mL) was stirred at room temperature and MsCl (278 mg, 2.4 mmol) was added dropwise. The reaction was stirred at room temperature for 8 h. The reaction was washed with 1N HCl and extracted with DCM, dried with Na2SO4 and concentrated to give 5-bromo-2-(4-cyanophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (260 mg, yield: 72%). MS (M+H)+: 448/450.

Workup

  1. stirringThe reaction was stirred at room temperature for 8 h
  2. washThe reaction was washed with 1N HCl
  3. extractionextracted with DCM
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8818ca3e7a6840658d68ddb89527d643
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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