Cesium carbonate → benzyl (1S,5S)-6-(5-cyano-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

The product of Example 52D (0.800 g, 3.40 mmol) in toluene (34 mL) was treated with 3-cyano-5-bromopyridine (0.690 g, 3.8 mmol), Pd2(dba)3 (0.0.64 g, 0.10 mmol), BINAP (0.086 g, 0.010 mmol) and Cs2CO3 (0.221 g, 6.80 mmol) and the reaction was heated at 80° C. for 12 hours. The mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 5% MeOH/CH2Cl2) to provide the title compound as a yellow oil (47%, 0.530 g). MS (DCI/NH3) m/z 335 (M+H)+.

Provenance & Evidence