Cesium carbonate → Ethyl 6-chloro-7-(4-(6-phenylpyrazin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled through a tetrahydrofuran (665 μl) solution of ethyl 7-(4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate (50 mg, 0.133 mmol; Example 45, step A) and 2-chloro-6-phenylpyrazine (25.4 mg, 0.133 mmol) at ambient temperature in a vial. Cesium carbonate (47.7 mg, 0.146 mmol), XPHOS ligand (12.7 mg, 0.0266 mmol), and tris(dibenzylideneacetone)dipalladium (0) (6.09 mg, 0.0066 mmol) were added. Argon was bubbled through the reaction for two minutes and the vial was capped. The reaction was heated to 60° C. (oil bath temperature) for 18 hours. The reaction was cooled to ambient temperature and applied to silica gel. Elution with a gradient of ethyl acetate/hexanes (20 to 85%) provided the title compound (65 mg, 92%) as an off-white solid.

Provenance & Evidence