7-Fluoro-2,3,4,9-tetrahydro-1H-beta-carboline → 7-fluoro-9H-beta-carboline

HRID 12177

Reaction equation

HRID 12177 reaction equation
[F:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][NH:9][CH2:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1>[Pd]>[F:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 150775507-Fluoro-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 221852527-fluoro-9H-beta-carbolineYield 88%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

7-fluoro-2,3,4,9-tetrahydro-1H-β-carboline (3.5 g, 18.42 mmol) was suspended in xylenes (60 ml) in a 250 ml round-bottom flask equipped with a condenser that was open to the atmosphere, and heated. To this hot reaction mixture was added Pd/C (10 wt %, 0.2 eq, 700 mg) and the mixture refluxed in xylenes overnight (12-14 hours). The solution was then filtered through a pad of celite and the collected filtrate was then evaporated on a rotary evaporator to give the desired product as a brown/tan solid (3.0 g, 88% yield).

Workup

  1. customequipped with a condenser that
  2. temperatureheated
  3. filtrationThe solution was then filtered through a pad of celite
  4. customthe collected filtrate was then evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-95c8195467304d848c25fbc20d6485d1
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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