Cesium carbonate → N-[6-(Methoxymethyl)-2-pyridinyl]-2,2-dimethylpropanamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-6-methoxymethylpyridine [1.00 g; J Heterocyclic Chem., 30, 563, (1993)], pivaloyl amide (0.756 g), palladium acetate (0.112 g), cesium carbonate (2.40 g), 4.5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.434 g) and 1,4-dioxan (5 ml) were sealed in a microwave vial and heated in a microwave oven with stirring for 30 minutes at 150° C. This process was repeated with a second batch of reagents and the products combined, the insoluble material filtered from solution and the filtrate evaporated under reduced pressure. The residue was purified by chromatography (silica; hexane/ethyl acetate) to afford the desired product as a yellow oil, 1.75 g. 1H NMR (CDCl3) δ: 9.84 (1H, s), 7.82 (1H, d), 6.87 (1H, d), 4.43 (2H, s), 3.48 (3H, s).

Provenance & Evidence