Cesium carbonate → HCID 11524375, compound

Participants

Reaction Steps

A mixture of Example 13 (500 mg, 1.37 mmol), 4-fluoro-3-methylaniline (206 mg, 1.64 mmol), Cs2CO3 (625 mg, 1.92 mmol), BINAP (85 mg, 0.37 mmol, 10 mol %) and Pd2(dba)3 (63 mg, 0.0685 mmol, 5 mol %) in toluene was heated at reflux for 18 h. A second charge of BINAP (42 mg, 5 mol %) and tris(dibenzylideneacetone)dipalladium(0) (31.5 mg, 2.5 mol %) was added and the mixture heated at reflux for a further 4 days. The mixture was partitioned between DCM (100 mL) and H2O (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (silica, 10% EtOAc in DCM) gave the title compound as an off-white solid (160 mg, 28%). δH (DMSO-d6) 9.39 (1H, s), 8.17 (1H, d, J 9.7 Hz), 7.87 (1H, dd, J 1.7, 7.9 Hz), 7.79 (1H, dd, J 2.1, 7.9 Hz), 7.75-7.66 (2H, m), 7.24-7.12 (3H, m), 6.71 (1H, d, J 9.7 Hz), 2.29 (3H, d, J 1.7 Hz). LCMS (ES+) RT 3.63 minutes, 410 (M+H)+.

Provenance & Evidence