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

HRID 276924
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 276924
[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.[C:16]1([C:22]#[C:23][C:24]2[N:25]=[N:26][C:27]([C:30]#[C:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:29]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].[NH2:39][N+:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[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:26][N:25]3[CH:24]=[CH:23][CH:22]=[CH:16][C:21]=23)=[CH:4][CH:3]=1.[C:16]1([C:22]#[C:23][C:24]2[N:25]=[N:26][C:27]([C:30]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:39][N:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=34)=[CH:28][CH:29]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
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Komponenten

9

Edukt 4

HCID 14798Sodium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 126802603-Chloro-6-(phenylethynyl)pyridazineHCID 126802613,6-Bis(2-phenylethynyl)pyridazine

Produkt 2

HCID 151581443-(3-Chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine
HCID 22629223
3-[3-(2-Phenylethynyl)pyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 4:1 mixture of 6-chloro-3-(2-phenylethynyl)pyridazine and 3,6-bis(2-phenylethynyl)pyridazine (10.2 g) was stirred in a two-phase mixture of N-aminopyridinium iodide (90% purity; 11 g), benzyltrimethylammonium chloride (1.4 g), sodium hydroxide (5.9 g), dichloromethane (51 ml), and water (51 ml) at ambient temperature for an hour. The reaction mixture was diluted with dichloromethane and water. The organic layer was separated, and the aqueous layer was extracted once with dichloromethane. The combined organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was subjected to 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 (0.72 g) and 3-[3-(2-phenylethynyl)pyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.5 g). Some fractions containing the mixture thereof were subjected to flash column chromatography on silica gel (elution with 50:1 dichloromethane-ethyl acetate) gave an additional product of 3-(3-chloropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.34 g) and 3-[3-(2-phenylethynyl)pyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.50 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted once with dichloromethane
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e9c6de11ff9c4910a215abf7d7cb93d0
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06355640B1

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