A mixture of 2-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (15 mg, 0.042 mmol), methylpropargyl ether (3.5 mg, 0.050 mmol), diisopropylethylamine (0.023 mL, 0.13 mmol), pyridine (0.011 mL, 0.13 mmol), catalytic amount of copper(I) iodide, tetrakis(triphenylphosphine)palladium(0) (9.6 mg, 0.0083 mmol) and N-methylpyrrolidinone (1 mL) was stirred for 4 hours at 120° C. After cooling, water and dichloromethane were added to the reaction solution for extraction, and the organic layer was filtered through a membrane filter. The solvent was evaporated in vacuo, then, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), trifluoroacetic acid salt of the title compound (1.5 mg, 0.00030 mmol, 7.2%) was obtained.
