1,10-Phenanthroline → Ethyl 4-(2-(ethyl(methyl)carbamoyl)pyrimidin-5-yloxy)-2-methylbenzofuran-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

The flask was charged with 5-bromo-N-ethyl-N-methylpyrimidine-2-carboxamide (SM-3: 615 mg, 2.5 mmol), ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (I-1c: 378 mg, 1.7 mmol), Cs2CO3 (1.15 g, 3.5 mmol), 1,10-phenanthroline (30.3 mg, 0.17 mmol), copper iodide (16 mg, 0.08 mmol) and dimethylformamide (17 mL). The reaction mixture was degassed with N2 for 5 minutes and then heated to 90° C. for 16 hours under a N2 atmosphere. The reaction mixture was diluted with ethylacetate (250 mL), washed with water (3×100 mL), dried (MgSO4) and concentrated. The crude material was purified by a biotage 50 g silica gel column (20%-100% EtOAc in Hep) to afford the title compound ethyl 4-(2-(ethyl(methyl)carbamoyl)pyrimidin-5-yloxy)-2-methylbenzofuran-6-carboxylate (I-5a: 180 mg, 28%) as a yellow solid.

Provenance & Evidence