Cesium carbonate → HCID 58065795, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-4-fluoro-5-nitroaniline (2.85 g, 12.13 mmol, 1.0 eq), isopropenylboronic acid pinacol ester (5.09 g, 30.33 mmol, 2.5 eq), Pd(OAc)2 (0.82 g, 3.64 mmol, 0.3 eq), Cy3P (1.70 g, 6.07 mmol, 0.5 eq) and Cs2CO3 (39.51 g, 121.28 mmol, 10 eq) in toluene (100 mL) and H2O (25 mL) was de-gassed with N2 for 15 minutes. The mixture was then heated at 100° C. (oil bath temperature). After allowing to cool to room temperature, the mixture was diluted with EtOAc (100 mL) and H2O (50 mL) and the mixture filtered through celite. The filter cake was washed with EtOAc (2×50 mL) and the filtrate partitioned. The organic layer was dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel (residue dry-loaded on to silica gel) using EtOAc/hexanes (1:5 gradient) as eluent to give the product (1.59 g, 64%) as a dark brown solid.

Provenance & Evidence