2-Chloromethyl 2-(trimethylsilyl)ethyl ether → ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-bromothiazole-4-carboxylate

Participants

Reaction Steps

To a mixture of compound 34B (0.815 g, 1.5 mmol) and SEMCl (0.318 mL, 1.8 mmol) in THF (6 mL) was added TEA (0.65 mL, 4.5 mmol) at rt. The reaction mixture was stirred for 20 minutes, concentrated under reduced pressure, and purified by column chromatography on silica gel eluting with 3:1/hexanes:EtOAc to provide 0.95 g of the desired product as a mixture of two inseparable isomers: MS (ESI(+)): m/z 657 (M+H).

Provenance & Evidence