Methanesulfonyl chloride → Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate

HRID 348960

Reaktionsgleichung

Reaktionsgleichung von HRID 348960
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:15][S:16]([NH:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)(=[O:18])=[O:17]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 14243967Methyl 4-amino-1H-indole-6-carboxylate

Produkt 1

HCID 21086208Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylateAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of methyl 4-amino-1H-indole-6-carboxylate (1.0 g) in DMF (10 mL) was added 4-dimethylaminopyridine (1.46 g) and methanesulfonyl chloride (0.6 g). The mixture was heated to 60° C. for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed three times with brine, dried over anhydrous sodium sulfate and concentrated to give 0.71 g of the title compound: 1H NMR (CDCl3) δ 3.02, 3.94, 6.69, 7.42, 7.81, 8.04.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bbf755d5c106475a89061efcce26d471
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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