Tricyclohexylphosphine → [5-(Oxetan-3-yl)pyridin-3-yl]boronic acid

HRID 1521598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521598
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH:7]=1.[B:12]1(B2OC(C)(C)C(C)(C)O2)[O:16]C(C)(C)C(C)(C)[O:13]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C([O-])(=O)C.[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:10]1[CH2:11][CH:8]([C:6]2[CH:7]=[C:2]([B:12]([OH:16])[OH:13])[CH:3]=[N:4][CH:5]=2)[CH2:9]1

Komponenten

7

Edukt 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 726987543-Bromo-5-(oxetan-3-YL)pyridine

Produkt 1

HCID 89961635[5-(Oxetan-3-yl)pyridin-3-yl]boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A vial containing the title compound from Example 63 Step A (45 mg, 0.21 mmol), bis(pinacolato)diboron (107 mg, 0.420 mmol), tris(dibenzylideneacetone)dipalladium (0) (38.5 mg, 0.042 mmol), tricyclohexylphosphine (23.6 mg, 0.084 mmol) and potassium acetate (61.9 mg, 0.631 mmol) in dioxane (1.0 mL) was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction was then passed through a syringe filter and concentrated under reduced pressure to provide the title compound which was used without further purification.

Aufarbeitung

  1. customwas flushed with nitrogen
  2. customsealed tightly
  3. customThe reaction was then passed through a syringe
  4. filtrationfilter
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bfb3c49e7d86446fbc4a28cdd1e56d9a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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