6-Fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one → 6-Fluoro-2,5-dihydro-5-methyl-1H-pyrido[4,3-b]indol-1-one

HRID 2081210Notes

Reaction equation

HRID 2081210 reaction equation
[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1>C(O)CO.[Pd]=O>[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH:12]=[CH:13][NH:14][C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 157125046-Fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 197992556-Fluoro-2,5-dihydro-5-methyl-1H-pyrido[4,3-b]indol-1-oneYield 100.9%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 174Ethylene GlycolSolvent

Procedure

A mixture of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (300 mg) and 10% palladium oxide on carbon catalyst (50% aqueous paste; 150 mg) in ethylene glycol (30 ml) was heated at reflux under nitrogen for 24 h. The cooled mixture was filtered and evaporated to give a solid (ca. 300 mg) which was purified by FCC eluting with System A (200:10:1) to give a solid (100 mg). A sample of this solid was further purified by HPLC on a Spherisorb 55W column, eluting with System A (95:5:0.5) at a flow rate of 15 ml/min to give the title compound, m.p. 294°-296°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 24 h
  3. filtrationThe cooled mixture was filtered
  4. customevaporated

Sources & evidence

ORD record
ord-eb80a79ce47e4337aa856254eb635ab5
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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