Sodium Carbonate → 1-(4-Methoxybenzyl)-4-phenylphthalazine

HRID 227761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227761
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](Cl)=[N:10][N:9]=2)=[CH:5][CH:4]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:10][N:9]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 866141621-Chloro-4-(4-methoxybenzyl)phthalazine

Produkt 1

HCID 667316721-(4-Methoxybenzyl)-4-phenylphthalazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 1,1′-bis(diphenylphosphoino)ferrocene-palladium dichloride (0.046 g, 0.063 mmol), 1-(4 -methoxybenzyl)-4-chlorophthalazine (0.360 g, 1.3 mmol), and phenylboronic acid (0.39 g, 3.2 mmol) was added dioxane (4.0 mL) and sodium carbonate (2.0M, aq)(1.9 ml, 3.8 mmol). The resulting mixture was heated to 100° C. in a sealed tube for 1 hour. The reaction was diluted with EtOAc and extracted with water and brine. The organic layers were dried over sodium sulfate, filtered, concentrated, and the crude was purified by ISCO silica gel chromatography (10-100% EtOAc/hexanes, 40 g column). Concentrated the product fractions to yield 1-(4-methoxybenzyl)-4-phenylphthalazine as a light yellow solid. MS m/z=327 [M+1]+. Calc'd for C22H18N2O: 326.40.

Aufarbeitung

  1. extractionextracted with water and brine
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe crude was purified by ISCO silica gel chromatography (10-100% EtOAc/hexanes, 40 g column)
  6. concentrationConcentrated the product fractions

Quellen und Nachweise

ORD-Eintrag
ord-9f8ec964df4948ada61aa90ef3b107d3
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560551B2

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