Cesium carbonate → HCID 67333799, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-bromo-5′-methyl-2,3′-bipyridine-4-carboxylate (2-1, 0.050 g, 0.156 mmol) in toluene (0.31 mL) at 25° C. was added pyrrolidine (0.026 mL, 0.311 mmol), BINAP (0.0096 g, 0.016 mmol) followed by Pd(OAc)2 (0.0035 g, 0.016 mmol) and cesium carbonate (0.076 g, 0.234 mmol) and the system was heated in the microwave reactor at 135° C. for 0.5 h. The system was partitioned between saturated aqueous sodium bicarbonate and EtOAc, washed with brine and dried over magnesium sulfate. Filtration and concentration followed by purification via normal phase chromatography (0→100% EtOAc in Hx) afforded a pale yellow oil. To this pale yellow oil (0.026 g, 0.083 mmol) in 1:1 THF/MeOH (0.40 mL) at 25° C. was added aqueous sodium hydroxide (0.0125 mL, 0.125 mmol, 10M) and the system was heated in the microwave reactor at 135° C. for 10 minutes. The solvents were removed in vacuo to afford the title compound (2-2) as a grey solid. ESI+MS C16H17N3O2: 284.2 found, 284.1 required.

Provenance & Evidence