Reaction #218

Reaction equation

Brc1cccc(OCc2ccccc2)

C1COCCN1

→

c1ccc(COc2cccc(N3CCO

Yield 86.9%

Solvents

Cc1ccccc1

Conditions

Procedure

Reagents split into 2 microwave tubes:- 2-(benzyloxy)-6-bromopyridine (2.641 g, 10.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.092 g, 0.10 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.093 g, 0.15 mmol) ,morpholine (1.045 g, 12.00 mmol) and sodium t-butoxide (1.345 g, 14.00 mmol) were suspended in toluene (30 mL). Degassed with N2 for 5 mins and sealed into a microwave tube. The reaction was heated to 120 °C for 10 minutes in the microwave reactor and cooled to RT. **_Work-up*_** The mixture was diluted with EtOAc and filtered through a short celite pad. The solution was then concentrated to dryness to give an orange viscous liquid (~4.7g). The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 4-(6-(benzyloxy)pyridin-2-yl)morpholine (2.350 g, 87 %) as a yellow oil.

Source