(2-Aminoethoxy)(tert-butyl)dimethylsilane → 4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-fluoroaniline

온도

120 °C

PdOAc2 (42.3 mg, 0.19 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (90 mg, 0.19 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (530 mg, 1.89 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (441 mg, 1.89 mmol) and cesium carbonate (921 mg, 2.83 mmol) in toluene (15 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 12 hours in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (50 mL), 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 purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 4-(benzyloxy)-N-(2-(tert- butyldimethylsilyloxy)ethyl)-3-fluoroaniline (312 mg, 44.1 %) as a yellow oil.

ORD 기록

ord-c8028b7fd0b24a71a931a3ca28fc4dd0

출처 데이터셋

750 AstraZeneca ELN dataset

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