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

HRID 595570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595570
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 903324155-bromo-2-(4-cyanophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamideAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8818ca3e7a6840658d68ddb89527d643
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242998B2

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