Tetrahydrofuran → 3-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-(phenylethynyl)pyridazine

HRID 46203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46203
ClC1N=[N:4][C:5]([CH2:8][C:9]2[CH:14]=[C:13]([C@H:15]3[C@H:20]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@@H:19]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:18]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[O:16]3)[CH:12]=[CH:11][C:10]=2[Cl:54])=CC=1.C([N:58](CC)[CH:59]([CH3:61])[CH3:60])(C)C.C#[C:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.O1CCC[CH2:73]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:54][C:10]1[CH:11]=[CH:12][C:13]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[CH:14][C:9]=1[CH2:8][C:5]1[N:4]=[N:58][C:59]([C:60]#[C:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:61][CH:73]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 86664426HCID 86664426, Verbindung

Produkt 1

HCID 672875763-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-(phenylethynyl)pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

To a mixture of Intermediate 6 (compound 24, 381 mg, 0.5 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (35 mg, 0.05 mmol) and copper(I) iodide (10 mg, 0.05 mmol) in tetrahydrofuran (10 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.5 mmol) and phenylacethylene (0.07 mL, 0.6 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was washed with water and brine prior to drying over magnesium sulfate. Filtration through a plug of silica gel and removal of the volatiles under reduced pressure yielded titled compound as a brown solid, which was used without further purification.

Aufarbeitung

  1. washAfter dilution with ethyl acetate, the organic layer was washed with water and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration
  4. customthrough a plug of silica gel and removal of the volatiles under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7e8229c8b0bc405aafc93935874746f9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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