Methanol → 2-(3-(4-Amino-6-chloropyridin-3-yl)prop-2-ynyl)-6-(thiophen-2-yl)pyridazin-3(2H)-one

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Reaction Conditions

Reaction Steps

A mixture of Et3N (200 μl, 1435 μmol), Cu(I) (10 mg, 53 μmol), PdCl2(PhP3)2 (20 mg, 28 μmol), 2-(prop-2-ynyl)-6-(thiophen-2-yl)pyridazin-3(2H)-one (90 mg, 416 μmol), and 2-chloro-5-iodopyridin-4-amine (138 mg, 542 μmol) in MeCN (1.5 mL) was heated to 80° C. under nitrogen for 1 h. The mixture was cooled to room temperature, and was loaded to a silica column. Chromatography with 0.5-5% MeOH in CH2Cl2 afforded a pink solid which was triturated with EtOAc-hexane (1:2, 10 mL) to give a pink solid as the pure product (48 mg). MS (ESI pos. ion) calc'd for C16H11ClN4OS: 342.0; found 343.1 (MH+). 1H NMR (400 MHz, Chloroform-d) δ ppm 5.18 (s, 2 H) 5.75 (br. s., 2 H) 6.64 (s, 1 H) 7.03 (d, J=9.78 Hz, 1 H) 7.11 (dd, J=5.09, 3.72 Hz, 1 H) 7.37-7.48 (m, 2 H) 7.73 (d, J=9.78 Hz, 1 H) 8.03 (s, 1 H).

Provenance & Evidence