Hydrochloric Acid → Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoat

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Reaction Conditions

Reaction Steps

To a -78° C. solution of the indole from Step 3 (3.1 g, 9.4 mmol) in 65 mL of THF was added KHMDS (0.6M toluene solution, 18.8 mL, 11.3 mmol) dropwise. The solution was warmed to 0° C., then cooled to -78° C. A solution of p-bromobenzyl bromide (3.0 g, 12.2 mmol) was then added, and the solution was allowed to warm to room temperature. The solution was then poured into 1M HCl and extracted with ether. The organic extracts were washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (20% ethyl acetate/hexanes) to provide 3.0 g of the title compound.

Provenance & Evidence