Potassium Carbonate → 4-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehyde

HRID 46395

Reaktionsgleichung

Reaktionsgleichung von HRID 46395
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](B(O)O)[CH:7]=1.Br[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=2)[CH:7]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 147614724-Bromopyridine-2-carbaldehydeHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 1360636234-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehydeAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(5-Chloro-2-hydroxyphenyl) boronic acid (1.58 g, 0.00914 mol) was combined with 4-bromopyridine-2-carbaldehyde (1.70 g, 0.0091 mol), bis(triphenylphosphine)palladium (II) chloride (0.321 g, 0.00046 mol) and potassium carbonate (3.16 g, 0.0228 mol) in a 5 mL microwave vial. 1,4-dioxane (3 mL) and water (0.2 mL) were added and heated to 100° C. for 50 minutes in the microwave. The reaction was diluted with ethyl acetate (30 mL) and water (20 mL), filtered, the organic phase was separated then dried over anhydrous sodium sulphate, concentrated in vacuo and purified by flash column chromatography, ISCO™ (80 g column, eluting with 100% heptane to 50% v/v ethyl acetate in heptane) to give the title compound as a beige solid (0.47 g).

Aufarbeitung

  1. filtrationfiltered
  2. customthe organic phase was separated
  3. dry with materialthen dried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography, ISCO™ (80 g column
  6. washeluting with 100% heptane to 50% v/v ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-63765137801a43b0b79bba7986e4c2d9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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