Water → N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]methanesulfonamide

HRID 1591823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591823
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[C:4]([F:16])[CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>N1C=CC=CC=1.C(OCC)(=O)C>[C:14]([C:11]1[N:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:3][C:4]=2[F:16])=[CH:9][CH:10]=1)#[N:15]

Komponenten

6

Edukt 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 160504325-(4-amino-2-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Produkt 1

HCID 16051367N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]methanesulfonamideAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-(4-amino-2-fluorophenyl)-1-methyl-1H-pyrrole-2-carbonitrile (0.20 g, 0.93 mmol) was dissolved in pyridine (2.0 mL). Methanesulfonyl chloride (0.07 mL, 0.9 mmol) was added and the mixture was stirred for 16 hours, followed by the addition of water. The mixture was diluted with ethyl acetate and then was washed with water, saturated CuSO4, 2N HCl, brine, dried over MgSO4, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane) to afford 0.18 g of N-[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-fluorophenyl]methanesulfonamide.

Aufarbeitung

  1. washwas washed with water, saturated CuSO4, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6d57220428844858a634e9d48cc56d37
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291643B2

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