Cesium carbonate → Tert-butyl (1r)-3-{6-chloro-5-[(e)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1h-indol-3-ylmethyl)propylcarbamate

Participants

Reaction Steps

A solution of Example 21C (100 mg, 0.35 mmol) in THF (3 mL) at 0° C. was treated with 9-BBN (0.5 M solution in THF, 0.70 mL, 0.35 mmol), stirred overnight while gradually warming to room temperature, cannulated into a mixture of Example 21B (108 mg, 0.32 mmol), PdCl2 (dppf) (26 mg, 0.032 mmol) and Cs2CO3 (228 mg, 0.7 mmol) in DMF, purged with nitrogen, and stirred at 50° C. for 8 hours. The mixture was treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The residual oil was purified by flash column chromatography on silica gel with 80% ethyl acetate/hexanes to provide the desired product (69 mg, 40%).

Provenance & Evidence