Morpholine → 5-(Morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (9.9 g, 50.25 mmol), morpholine (7.96 mL, 100.49 mmol), sodium 2-methylpropan-2-olate (19.32 g, 200.98 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (1.172 g, 2.51 mmol) in degassed dioxane (200 mL) was added diacetoxypalladium (1.128 g, 5.02 mmol) and the reaction mixture was heated under nitrogen at 90 °C for 17 hours, then evaporated and partitioned between DCM (150 ml) and saturated aqueous sodium bicarbonate solution (150 mL). The aqueous phase was extracted further with DCM (70 ml) 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 (8.54 g, 84 %) as a yellow solid.

Provenance & Evidence