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

HRID 1632816Notes

Reaction equation

HRID 1632816 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 with hexane by distillation to a final pot temperature 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. distillationdisplaced with hexane by distillation to a final pot temperature 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-0e2fcfe116be4b2882dd063b95bb7969
Source dataset
uspto-grants-1984_10
Patent number
US04477669

Reaction notes

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