Water → HCID 67209520, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromo-5-methyl-pyridine-2-carboxylic acid methyl ester (1.6 g, 6.945 mmol), methylacrylate (1.50 g, 17.39 mmol), allylpalladium(II) chloride dimer (0.127 g, 0.348 mmol), tri-o-tolylphosphine (0.212 g, 0.695 mmol), water free sodium carbonate (2.211 g, 20.9 mmol), and N,N.dimethylacetamide (4.56 ml) were added to toluene (15 ml) and the reaction mixture was stirred for 18 h at 115° C. in a microwave apparatus. The mixture was diluted with EtOAc, washed with brine, dried over sodium sulfate, and the solvents were evaporated under reduced pressure. The residue was purified by chromatography on silica (Flashmaster, hex to hex/EtOAc 2/3 over 40 min, 20 min hex/EtOAc 2/3) to give the product as off-white solid (1.31 g, 80%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.51 (s, 1H), 8.20 (s, 1H), 8.10 (d, 1H), 6.69 (d, 1H), 3.88 (s, 3H), 3.74 (s, 3H), 2.39 (s, 3H); LCMS RtL=2.753 min; [M+H]+=236.0]

Provenance & Evidence