Ethyl diazoacetate → Ethyl 2-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]cyclopropanecarboxylate

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To a room temperature solution of the indole from Step 1 (3.91 g, 11.0 mmol) in 20 mL toluene was added rhodium (II) octanoate dimer (109 mg, 0.14 mmol), and the solution was cooled to 0° C. A solution of ethyl diazoacetate (3.0 mL, 28.5 mmol) in 13 mL toluene was then added via syringe pump at 1.2 mL/hr. Fresh catalyst was then added along with an additional 1 mL ethyl diazoacetate in toluene over 2.5 h. The crude reaction mixture was applied directly to a silica gel column and eluted with 1% to 2.5% ethyl acetate/toluene. 1.1 g of the trans isomer of the title compound was thus obtained, followed by 1.2 g of the cis isomer of the title compound.

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