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Hydrochloric Acid → 3-(3-Chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 276923
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 276923
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[I-].[NH2:17][N+:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O.ClCCl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[C:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 126802603-Chloro-6-(phenylethynyl)pyridazine

Produkt 1

HCID 151581443-(3-Chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963
Benzyltrimethylammonium chloride
Katalysator
HCID 962WaterLösungsmittel2×
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a two-phase mixture of 6-chloro-3-(2-phenylethynyl)pyridazine (2.3 g), N-aminopyridinium iodide (90% purity; 5.3 g), benzyltrimethylammonium chloride (0.2.0 g), dichloromethane (23 ml), and water (23 ml) was added sodium hydroxide (3.4 g) in one portion. After stirring at ambient temperature overnight, the reaction mixture was treated with concentrated hydrochloric acid followed by dilution with dichloromethane and water. The organic layer was separated, and the aqueous layer was extracted once with dichloromethane. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with 25:1 dichloromethane-ethyl acetate) to give 3-(3-chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.92 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted once with dichloromethane
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (elution with 25:1 dichloromethane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bf92e9a9e01343b0ad6dce274b2a6a20
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06355640B1

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