Hydrogen Peroxide → HCID 68513273, compound

Participants

Reaction Steps

To a stirred solution of 4-(1-(4-methoxybenzyl)-3-vinyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (1.17 g, 3.00 mmol) in THF (5 mL) was added 9-BBN (24.0 ml, 12.0 mmol, 0.5 M in THF). The reaction was stirred for 18 hours at room temperature. The reaction was chilled (submerged in an ice bath) and then quenched by addition of 5N aqueous sodium hydroxide (6.00 mL, 30.0 mmol). After stirring for 30 minutes in the ice bath, 30% aqueous hydrogen peroxide (2.88 mL, 30.0 mmol) was added. After stirring for 5 minutes at 0° C., the reaction was allowed to stir for 30 minutes at room temperature. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The phases were separated, and the aqueous phase was re-extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated. The crude was purified by Biotage Flash 40M, eluting with 2% MeOH in DCM (2 L). The product was obtained as a waxy solid (1.0 g, 78%).

Provenance & Evidence