Sodium hydride → HCID 4657444, compound

Participants

Reaction Steps

5-Bromoindole (1.96 g, 10 mmol) was dissolved in 20 mL of DMF, 60%-NaH (0.44 g, 11 mmol) was added. It was stirred for 30 minutes, then 2-fluorobenzyl bromide (1.33 mL, 11 mmol) was added. Stirring continued at 50° C. for 5 hours. After dilution with EtOAc, the organic layer washed with brine (5×), dried over MgSO4. After evaporation to dryness, it was then dried under high vacuum to yield N-2-Fluorobenzyl-5-bromoindole in quantitative yield. The title compound was prepared by substituting N-2-Fluorobenzyl-5-bromoindole (3.04 g, 10 mmol) for 4-bromo-2-nitrophenylamine in EXAMPLE 2A. Crude material was purified by silica gel column chromatography, eluting with 2.5% EtOAc in hexane. 2.18 g of the title compound was obtained. MS: ESI(+) m/e 352.1 (M+H)+.

Provenance & Evidence