Triethylamine → HCID 54718752, compound

Participants

Reaction Conditions

Reaction Steps

4-hydroxy-3-(5-iodo-4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (200 mg, 0.48 mmol, Example 222) was dissolved in DMF (2.4 ml). Et3N 0.133 ml, 0.96 mmol) and methyl propargyl ether (0.202 ml, 2.4 mmol) were added and the mixture was degassed with N2 for 2 min. CuI (9.1 mg, 0.048 mmol) and PdCl2(PPh3)2 (17 mg, 0.024 mmol) were added, the vessel was capped and the reaction was heated at 60° C. with stirring for 2.5 h. The reaction mixture was then cooled and filtered through a plug of silica gel eluting with CH2Cl2→EtOH. The organics were removed by rotary evaporation and the residue was purified by RP-HPLC to give the title compound. MS (ESI) m/z 357.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.49 (s, 1H), 6.92 (s, 1H), 4.38 (s, 3H), 2.23 (s, 3H).

Provenance & Evidence