Cesium carbonate → HCID 86677027, Verbindung

HRID 927078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927078
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH2:45])O1>C([P+]([Pd](Cl)(Cl)[P+](C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C.O>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH2:45])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2×

Produkt 1

HCID 86677027HCID 86677027, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178482902HCID 178482902, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1: 3 g, 9.18 mmol), dioxane (32.1 ml) and water (9.64 ml) was degassed and to this was added mono(bis(di-tert-butyl(4-(dimethylamino)phenyl)phosphonio)palladium(IV)) dichloride (0.195 g, 0.275 mmol), cesium carbonate (10.14 g, 31.1 mmol) and 4,4,5,5-tetramethyl-2-(1-phenylethenyl)-1,3,2-dioxaborolane (3 g, 13.04 mmol). The mixture was heated to 80° C. for 6 hours and upon cooling was partitioned between dichloromethane and water. The organic portion was dried (MgSO4), filtered and concentrated to give an orange oil. The crude oil was purified by silica chromatography eluting with 0-60% ethyl acetate in petrol to afford 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine as a brown oil (yield=91%).

Aufarbeitung

  1. customwas degassed
  2. temperatureupon cooling
  3. customwas partitioned between dichloromethane and water
  4. dry with materialThe organic portion was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange oil
  8. customThe crude oil was purified by silica chromatography
  9. washeluting with 0-60% ethyl acetate in petrol

Quellen und Nachweise

ORD-Eintrag
ord-383d0179d62c48d9821b288ebf108a23
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290456B2

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