Pyridine → HCID 17882414, Verbindung

HRID 618339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618339
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:23])[C:12]([C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][CH:14]=1)[NH2:5].N1C=CC=CC=1.[C:30]([O:33][CH2:34][CH2:35][S:36](Cl)(=[O:38])=[O:37])(=[O:32])[CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:36]([CH2:35][CH2:34][O:33][C:30](=[O:32])[CH3:31])(=[O:38])=[O:37])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:23])[C:12]([C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 131390002-(chlorosulfonyl)ethyl acetateHCID 70102005HCID 70102005, Verbindung

Produkt 1

HCID 17882414HCID 17882414, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Fluoro-4-[5-benzoyl-1-methyl-1H-pyrrol-2-ylmethyl]aniline (0.75 g, 2.43 mmol) [prepared as described in Example 1, but substituting ethyl 1,4-dimethylpyrrole-2-acetate with methyl 1-methylpyrrole-2-acetate in Step (a)], and pyridine (0.39 ml, 4.88 mmol) were dissolved in methylene chloride (8 ml). 2-Acetoxyethanesulfonyl chloride (681 mg, 3.65 mmol) was added to the solution and after 15 min, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to dryness. Purification of the residue by flash chromatography (hexane-ethyl acetate, 3:2) gave N-{3-fluoro-4-[5-benzoyl-1-methyl-1H-pyrrol-2-ylmethyl]-phenyl}-2-(acetoxy)ethanesulfonamide, (643 mg, 58%) as a solid. ##STR58##

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification of the residue by flash chromatography (hexane-ethyl acetate, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-ce30859d44ed4320b8cf9280e12567ba
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952368

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