Acetonitrile → 5-(N-methyl-3-tert-butoxycarbonylaminopropyn-1-yl)-benzene-1,3-dicarboxylic acid diethyl ester

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Reaction Steps

5-Trifluoromethanesulfonyloxy-isophthalic acid dimethyl ester (Bodwell, G. J. Fleming, J. J.; Mannion, M. R.; Miller, D. O. J. Org. Chem. 2000, 65 (17), 5360) (1 g) was dissolved in 2 mL of acetonitrile. N-Methyl-N-tert-butoxycarbonyl-propargylamine (Bradbury, B. J.; Baumgold, J.; Jacobsen, K. A. J. Med. Chem. 1990, 33 (2), 741) (643 mg), bis(triphenylphosphine)palladium chloride (205 mg), copper iodide (56 mg) and triethylamine (591 mg) were added. The resultant mixture was stirred for 15 h at room temperature. The solvent was removed by evaporation under reduced pressure and the residue was then washed into separatory funnel using ethyl acetate and water. The layers were separated, and the aqueous layer was extracted once with ethyl acetate. The combined organic solutions were washed with a saturated sodium chloride aqueous solution, dried over magnesium sijlphate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Biotage FLASH 40+M 100 g column, SiOH 32-63 μm, eluted with ethyl acetate/heptane, 20:80) to give 5-(N-methyl-3-tert-butoxycarbonylaminopropyn-1-yl)-benzene-1,3-dicarboxylic acid diethyl ester (896 mg):

Provenance & Evidence