4-Bromobenzyl bromide → Ethyl 2-(1-(4-bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

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Reaction Steps

To the ethyl ester from Example 7, Step 1 (2.00 g, 8.10 mmol) dissolved in THF (40.0 mL) was added at -78° C. a 0.5M solution of KHMDS (16.0 mL, 8.10 mmol) in toluene and HMPA (200 μL). After a period of 10 min, 4-bromobenzyl bromide was added to the resulting mixture. The reaction mixture was brought to room temperature, quenched by the addition of 25% aqueous NH4OAc solution, extracted with EtOAc, dried over Na2SO4 and evaporated in vacuo. The title product was purified by flash chromotography (15% to 20% EtOAc in hexane) (1.5 g).

Provenance & Evidence