Water → 1-(3-(Benzyloxy)propyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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Reaction Conditions

Reaction Steps

A solution of 4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (8.47 g, 43.6 mmol) in DMF (85 mL) was treated with 1-bromo-3-benzyloxypropane (10.0 g, 43.6 mmol) and Cs2CO3 (14.2 g, 43.6 mmol). This mixture was heated to 90° C. and allowed to stir under N2 overnight. The reaction mixture was poured into water and extracted twice with EtOAc. The combined organic layers were washed with water 3 times, once with brine, dried over Na2SO4, filtered and concentrated to an orange oil which was purified on a Teledyne ISCO Combiflash® Rf system (0-30% EtOAc/DCM) to afford the title compound as 8.5 g of a clear oil (57%). 1H NMR (400 MHz, CDCl3) δ 7.79 (s, 1H), 7.66 (s, 1H), 7.29-7.40 (m, 5H), 4.48 (s, 2H), 4.26 (t, J=6.8 Hz, 2H), 3.43 (t, J=5.9 Hz, 2H), 2.16 (quin, J=6.3 Hz, 2H), 1.60 (dd, J=6.6, 8.6 Hz, 2H), 1.33 (s, 12H).

Provenance & Evidence