Cesium carbonate → HCID 86603157, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6,N-dimethoxy-N-methyl-isonicotinamide (1.0 g, 4.35 mmol) was added to a mixture of Pd(OAc)2 (0.05 g, 0.22 mmol), BINAP (0.27 g, 0.43 mmol), benzophenone imine (0.88 mL, 5.22 mmol), and cesium carbonate (7.08 g, 21.7 mmol) in toluene (16 mL) and heated to 100° C. for 12 h. Pd(OAc)2 (0.05 g, 0.22 mmol) was added to the reaction mixture and stirred for an additional 1 h at 100° C. The reaction mixture was cooled to room temperature, quenched with EtOAc (200 mL), and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (ethyl acetate/hexanes 65:35) to afford the title compound as a yellow oil (1.53 g, 94%). MS: 376.3 (MH+); HPLC Rf: 6.92 min. (HPLC method 4).

Provenance & Evidence