Acetyl chloride → 1-[3-Bromo-6-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-2-fluoro-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Participants

Reaction Steps

In a manner similar to the method described in example 1d, 4-(4-bromo-3-fluoro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (4.22 g, 10.5 mmol) was used as the starting material in place of 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester to react with 1,1,3,3,3-hexamethyldisilazane (2.18 mL, 10.5 mmol), n-butyllithium (2.5 M, 4.2 mL, 10.5 mmol), trimethylsilyl chloride (1.33 mL, 10.5 mmol), triethylamine (1.9 mL, 13.6 mmol) and acetyl chloride (0.97 mL, 13.6 mmol) to give crude 1-[3-bromo-6-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-2-fluoro-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Provenance & Evidence