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

HRID 552198Notes

Reaction equation

HRID 552198 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-])=O)[C:14]=1[F:15])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:16])[C:14]=1[F:15])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 1

HCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 671655216-chloro-7-fluoro-9H-beta-carbolin-8-ylamineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. customthe reaction vessel was flushed with hydrogen
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46aa6fc71b8847c58b77e84ef26e2673
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

Loading…