5-Bromo-2-methoxybenzonitrile → (R)-5-(2-(tert-butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

Trial reaction for PdOAc2 (0.021 g, 0.09 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.045 g, 0.09 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (0.200 g, 0.94 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.214 g, 1.13 mmol) and cesium carbonate (0.461 g, 1.41 mmol) in toluene (10 mL) at 20°C in a microwave vial. The reaction mixture was diluted with EtOAc (20 mL) and water (20 mL). The biphasic mixture was filtered through celite. The organic layer was separated and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was filtered and dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was evaporated and was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford (R)-5-(2-(tert- butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile (0.188 g, 62.2 %) as a orange oil. repated on a lager scale in RSL - See EN04063-90

Provenance & Evidence