Hexane → (1-{[2-(Trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

A hexane solution of n-BuLi (60 mL, 150.97 mmol) was added slowly to a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (25.0 g, 100.65 mmol) in dry THF (200 mL) at −70° C. under N2 protection. The mixture was stirred at −45° C. for 2 hour. After (i-PrO)3B (30.29 g, 161.03 mmol) was added, the mixture was stirred overnight warming to RT. Then the reaction mixture was quenched with 1M aqueous HCl and extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4, filtered and the solvent was concentrated in vacuo under reduced pressure. The crude product was purified using column chromatography (petroleum ether:EtOAc=5:1) to provide the product of (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid (14.4 g, yield: 49%). 1H-NMR (CDCl3, 400 MHz) δ 8.49 (dd, J=4.8 Hz, 1.6 Hz, 1H), 8.07 (dd, J=8.0 Hz, 1.6 Hz, 1H), 7.21 (dd, J=8.0 Hz, 4.8 Hz, 1H), 6.92 (s, 1H), 6.02 (s, 2H), 3.74 (t, J=8.4 Hz, 2H), 1.08 (t, J=8.4 Hz, 2H), 0.04 (s, 9H). MS (M+H)+: 293.

Provenance & Evidence