Triisopropyl borate → 5-(1-(Tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-fluoropyridin-3-ylboronic acid

HRID 1621899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621899
C([Li])CCC.[Si:6]([O:13][CH2:14][C:15]([C:18]1[CH:19]=[CH:20][C:21]([F:24])=[N:22][CH:23]=1)([CH3:17])[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C>C1COCC1>[Si:6]([O:13][CH2:14][C:15]([C:18]1[CH:19]=[C:20]([B:25]([OH:30])[OH:26])[C:21]([F:24])=[N:22][CH:23]=1)([CH3:17])[CH3:16])([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 21531Triisopropyl borateHCID 666006945-(1-(Tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-fluoropyridineHCID 178418339Butyllithium

Produkt 1

HCID 665999945-(1-(Tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-fluoropyridin-3-ylboronic acidAusbeute 108 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (1.66 M in hexane) (Aldrich, St. Louis, Mo.; 0.429 mL, 0.712 mmol) was added (dropwise over 1 min) to a solution of 5-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-fluoropyridine (183.5 mg, 0.647 mmol) in THF (3.3 mL) at −78° C., and the resulting yellow solution was stirred at −78° C. for 1 h. Tri-isopropyl borate (Aldrich, St. Louis, Mo.; 0.179 mL, 0.777 mmol) was then added, and the resulting mixture was stirred at −78° C. for 1 h. The reaction mixture was subsequently partitioned between EtOAc (50 mL) and water (30 mL) (1 N HCl (about 200 μL) was added to bring the pH of the aqueous layer to 6.5). The organic layer was separated, and the aqueous layer was extracted with EtOAc (30 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 5-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-fluoropyridin-3-ylboronic acid (228.0 mg, 0.697 mmol, 108% yield) as a colorless oil. m/z (ESI, +ve) 328.3 (M+H)+.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at −78° C. for 1 h
  2. customThe reaction mixture was subsequently partitioned between EtOAc (50 mL) and water (30 mL) (1 N HCl (about 200 μL)
  3. additionwas added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (30 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7788acb534ec4ce1a8ca14a0c13f01ab
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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