Allyl bromide → 1-(Prop-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reaktionsgleichung

[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.[CH2:15](Br)[CH:16]=[CH2:17].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>>[CH2:17]([N:2]1[CH:3]=[C:4]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:13])([CH3:12])[O:14]2)[CH:5]=[N:1]1)[CH:16]=[CH2:15]

Komponenten

Edukt 3

HCID 7841Allyl bromide

HCID 2724254Sodium bis(trimethylsilyl)amide

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 583546341-(Prop-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Versuchsvorschrift

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and allyl bromide according to Method AC (after initial stirring at r.t. for 16 h, an additional 0.3 equivalent of sodium bis(trimethylsilyl)amide was added and the reaction mixture was stirred at 90° C. for 16 h) and was isolated as an amber oil (quantitative) that was used without further purification. LCMS (ES+) 235.0 (M+H)+, RT 3.09 minutes (Method 1).