Sodium hydride → 4-Bromo-1-[(3-fluorophenyl)methyl]-1H-indole-2,3-dione

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Reaction Steps

4-Bromo-1H-indole-2,3-dione (6.38 g) was dissolved in 100 mL of DMF and at 0° C., and 60% NaH (1.32 g) was added in portions. The mixture was stirred for 20 minutes before adding 3-fluorobenzyl bromide. The solution was stirred for approximately 30 minutes, quenched with water, and partitioned between water and diethyl ether. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to yield 9.18 g 4-Bromo-1-(3-fluoro-benzyl)-1H-indole-2,3-dione that was sufficiently pure for use in step 2 below. MS: 385 (M+H)+.

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