6-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole → 6-chloro-7-fluoro-9H-beta-carbolin-8-ylamine

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Reaction Steps

A slurry of 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.88 mmol) in MeOH (25 ml) was degassed with argon. Palladium on charcoal (20% w/w on C, 50 mg) was added and the reaction vessel was flushed with hydrogen. The slurry was stirred under a balloon of hydrogen for 6 hr, then filtered through celite and concentrated under reduced pressure to yield 6-chloro-7-fluoro-9H-β-carbolin-8-ylamine (400 mg) as a brown solid. 1H-NMR (300 MHz, DMSO-d6): δ 11.48 (br s, 1); 8.99-8.98 (m, 1); 8.37-8.35 (m, 1); 8.11-8.09 (m, 1); 7.74-7.72 (m, 1); 5.65 (br s, 2). HCOOH standard conditions. DAD Rf=1.00 min. MS (M+H+): 236.

Provenance & Evidence