HCID 13374324, compound → 8-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 358388Notes

Reaction equation

HRID 358388 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]3[CH2:18][CH2:19][N:20](C(OCC4C=CC=CC=4)=O)[CH2:21][C:5]=3[C:4]=2[CH:3]=1>C(OCC)(=O)C.CO.[Pd]>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:6]3[CH2:18][CH2:19][NH:20][CH2:21][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 13374324HCID 13374324, compound

Product 1

HCID 126299068-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a Parr bottle were combined 5% Pd/C (10 g of 50% water-wet) and 60 g of 8-fluoro-5-(p-fluorophenyl)-2-carbobenzoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole (60 g, 0.143 mole) in 400 ml ethyl acetate and 100 ml methanol and the mixture hydrogenated at 44-80 psig for 4 hours. Catalyst was recovered by filtration and the filtrate evaporated to solids in vacuo. The residue taken into CH2Cl2, carbon treated, dried (Na2SO4) and CH2Cl2 displaced and hexane by distillation to a final pot temperture of 70° C. The white, crystalline product was recovered by filtration, 35.6 g, m.p. 126°-129° C.

Workup

  1. filtrationCatalyst was recovered by filtration
  2. customthe filtrate evaporated to solids in vacuo
  3. additiontreated
  4. dry with materialdried (Na2SO4) and CH2Cl2
  5. distillationhexane by distillation to a final pot temperture of 70° C
  6. filtrationThe white, crystalline product was recovered by filtration, 35.6 g, m.p. 126°-129° C.

Sources & evidence

ORD record
ord-25ccbb0c7b834499b0872f5f162fee10
Source dataset
uspto-grants-1984_08
Patent number
US04467090

Reaction notes

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