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| Typical applications of Bredereck's reagent（CAS:5815-08-7）（9） |
| 2022-06-20 |
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5-Benzyloxy-6-fluoroindole (CAS: 145159-66-6)
A suspension of 10.55 g (40.4 mmol, 1 eq.) of Intermediate 92 in 13.5 mL (64.6 mmol, 1.6 eq.) of bis-dimethylamino-t-butoxymethane was stirred at 90 °C overnight.
The resulting red-orange solid was dried in vacuum and redissolved in 250 mL of 1/10 mixture of ethanol/dioxane and ~ 1 g of Raney nickel was added.
The compound was hydrogenated using hydrogen gas at room temperature for 5 hours.
The catalyst was filtered off over celite and the solvents were evaporated to give the crude indole as dark brown oil.
The crude product was chromatographed on silica gel using CH2Cl2 as eluent to yield 2.2 g (9.1 mmol) as yellow solid (yield 23%).
The compound can be additionally purified by recrystallyszation from CH2Cl2/zso-hexane. MS (ESI+) for Ci5Hi2FNO m/z 242 (M+H)+.
Ref: WO2008/3703, 2008, A1
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