Propargyl alcohol → ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxyprop-1-ynyl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 34C (0.38 g, 0.564 mmol), prop-2-yn-1-ol (0.047 g, 0.846 mmol), CuI (0.011 g, 0.056 mmol), Et3N (1.57 mL, 11 mmol) and Pd(PPh3)2Cl2 (0.02 g, 0.028 mmol) in DMF (2 mL) was heated at 90° C. for 2 hours. After cooling, the reaction mixture was diluted with CH2Cl2. The solid was filtered off. The filtrate was concentrated. The residue was purified by flash column chromatography on silica gel eluting with 3:2/hexanes:EtOAc to provide 0.19 g of the desired product 36B as a mixture of two inseparable isomers: MS (ESI(+)): m/z 649 (M+H).

Provenance & Evidence