Cesium carbonate → HCID 22736995, compound

Participants

Reaction Steps

To a stirred solution of 4.70 g (20.0 mmol) 4-bromo-2-nitro-anisole in 100 ml dioxane were added 4.03 g (24.3 mmol) methyl-(tetrahydro-pyran-4-ylmethyl)-amine hydrochloride (1:1), 0.710 g (20.0 mmol) 2-(dicyclohexylphosphino)biphenyl, 16.5 g (50.65 mmol) cesium carbonate, and 227 mg (1.0 mmol) palladium (II) acetate. The mixture was heated at reflux for 24 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/1 hexane/ethyl acetate) afforded 3.5 g (62%) (4-methoxy-3-nitro-phenyl)-methyl-(tetrahydro-pyran-4-ylmethyl)-amine as a red oil. ES-MS m/e (%): 281 (M+H+, 100).

Provenance & Evidence