反応 #676

ord-c34fe67f0c724f1db0a5e6644d227638

反応方程式

Brc1cnc2[nH]ccc2c1
Brc1cnc2[nH]ccc2c1
C1COCCN1
C1COCCN1
c1cc2cc(N3CCOCC3)cnc2[nH]1
c1cc2cc(N3CCOCC3)cnc
収率 64.6%

溶媒

反応条件

温度
90°CELSIUS

実験手順

To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (5.1 g, 25.88 mmol), morpholine (4.10 mL, 51.77 mmol), sodium 2-methylpropan-2-olate (9.95 g, 103.54 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (0.604 g, 1.29 mmol) in degassed dioxane (100 mL) was added diacetoxypalladium (0.581 g, 2.59 mmol) and the reaction mixture was heated under nitrogen at 90 °C for 17 hours, then evaporated and partitioned between DCM (80ml) and saturated aqueous sodium bicarbonate solution (80ml). The aqueous phase was extracted further with DCM (50ml) and the combined organics were evaporated, redissolved in a mixture of methanol and DCM and purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-(1H-pyrrolo[2,3-b]pyridin-5-yl)morpholine (3.40 g, 64.6 %) as a yellow solid.

出典

750 AstraZeneca ELN dataset