Morpholine → HCID 68733191, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-2′-fluoro-4′-methylbiphenyl-3-carboxylate (408.0 mg, 1.263 mmol) in N,N-dimethylacetamide (5 mL) was added morpholine (0.17 mL, 1.9 mmol), cesium carbonate (1.23 g, 3.79 mmol), palladium dibenzylidene acetone (116.0 mg, 0.13 mmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′biphenyl (XPhos; 90.0 mg, 0.19 mmol) and the mixture heated to 100° C. After 16 h the reaction was allowed to cool to ambient temperature, filtered with methanol, and sodium hydroxide (1M in water; 3.0 mL, 3.0 mmol) was added. After 16 h, reaction was concentrated, acidified with trifluoroacetic acid, and purified by reverse phase HPLC (C-18, 95% water/acetonitrile→20% water/acetonitrile with 0.1% trifluoroacetic acid). Extraction with dichloromethane and 1M aqueous hydrochloric acid gave the title compound. MS 316.1 (M+1).

Provenance & Evidence