2-Chloro-5-pyridinesulfonyl chloride → HCID 86630978, Verbindung

HRID 1782301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1782301
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1.[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22]([N:12]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:9][C:10]([CH:13]=[O:14])=[CH:11]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Komponenten

3

Edukt 2

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 469085935-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde

Produkt 1

HCID 86630978HCID 86630978, Verbindung

Versuchsvorschrift

By a similar reaction as in Reference Example 65 and using 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) and 6-chloropyridine-3-sulfonyl chloride (1.30 g), the title compound was obtained as a pale-red solid (yield 1.14 g, 66%). More specifically, 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (893 mg) was dissolved in tetrahydrofuran (10 mL), sodium hydride (60% in oil, 226 mg) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (1.1 mL) was added and the mixture was further stirred at the same temperature for 15 min. 6-Chloropyridine-3-sulfonyl chloride (1.30 g) was added. The reaction mixture was stirred at room temperature for 15 min. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:2) to give the title compound as a pale-red solid (yield 1.14 g, 66%).

Aufarbeitung

  1. customBy a similar reaction as in Reference Example 65

Quellen und Nachweise

ORD-Eintrag
ord-d9c6dc74a8624dce83e08f84ae62bccf
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498337B2

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