Sodium Carbonate → HCID 86590138, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl (3,5-dibromo-4-pyridyl)carbamate (4.2 g; 12.0 mmol), phenylboronic acid (1.76 g; 14.4 mmol), sodium carbonate (3.1 g; 29.2 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.416 g; 0.36 mmol) in dioxane (24 ml) and water (12 ml) is heated at 70° C. under argon for 8 hours. The reaction mixture is concentrated under reduced pressure. The residue obtained is taken up in ethyl acetate (200 ml), washed with water (2×100 ml) and brine (100 ml), dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue is chromatographed on a column of silica, eluting with an ethyl acetate/cyclohexane gradient of from 0 to 5%. 2.3 g of 1,1-dimethylethyl (3-bromo-5-phenylpyrid-4-yl)carbamate are isolated in the form of a white solid.

Provenance & Evidence