Cesium carbonate → 1,1-Dimethylethyl (6-formyl-3-pyridinyl)methylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-pyridinecarbaldehyde (1.5 g, 8.064 mmol), 1,1-dimethylethyl methylcarbamate (D83) (1.267 g, 9.677 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.148 g, 0.161 mmol), xantphos (0,373 g, 0.645 mmol) and cesium carbonate (3.678 g, 11.289 mmol) in dioxane (35 mL) was heated at 110° C. overnight under an argon atmosphere. On cooling, the solvent was removed in vacuo and the residue partitioned between EtOAc and water. The organic layer was separated, washed with water and brine, dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-50% ether/petroleum ether gave the title compound as a brown oil (0.977 g). δH (CDCl3, 400 MHz) 10.01 (1H, s), 8.79 (1H, d), 7.94 (1H, d), 7.86 (1H, dd), 3.40 (3H, s), 1.53 (9H, s). MS (ES+): 259.1 (MNa+), 181.2, no molecular ion (MH+) observed.

Provenance & Evidence