Methanol → 6-(Dimethylamino)pyridine-3-boronic acid

HRID 57528

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[Li]CCCC.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.CO>C1COCC1>[CH3:9][N:8]([CH3:10])[C:5]1[N:6]=[CH:7][C:2]([B:16]([OH:21])[OH:17])=[CH:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: -72 °C

Versuchsvorschrift

A solution of 5-bromo-N,N-dimethylpyridin-2-amine (500 mg, 2.5 mmol) in THF (10 mL) was treated with n-BuLi (1.2 mL, 3 mmol) at −72° C. for 2 hours. Triisopropyl borate (705 mg, 3.75 mmol) was then added dropwise. After the completion of the addition, the mixture was stirred at −72° C. for an additional 1 hour and slowly warmed up and stirred at the ambient temperature overnight. MeOH was carefully added, and the volatiles were removed under reduced pressure to give the title compound. MS (m/z): 167 (M+H)+.

Aufarbeitung

additionAfter the completion of the addition
temperatureslowly warmed up
stirringstirred at the ambient temperature overnight
customthe volatiles were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-1d1e0032d13f4159b2fc306ea574db4d
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434726B2

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