Trifluoroacetic acid → Trifluoroacetic acid

HRID 885077Notes

Reaction equation

HRID 885077 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[N:13][C:14]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9]1)C1C=CC=CC=1.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>CO.[Pd]>[C:18]1([C:14]2[N:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[CH2:16][CH2:17][NH:8][CH2:9]3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58026046HCID 58026046, compound

Product 2

HCID 6422Trifluoroacetic acidYield 100%HCID 58026061HCID 58026061, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-benzyl-5-phenyl-1,2,3,4-tetrahydro-2,6-naphthyridine, 2 TFA (0.48 g, 0.908 mmol) in MeOH (10 mL) was added Pd/C (0.193 g, 0.182 mmol). The mixture was flushed with N2, then was purged with H2 and stirred at rt under 1 atm. After stirring the reaction for 3 h it was filtered through a pad of CELITE®. The organic solution was concentrated under reduced pressure to give 5-phenyl-1,2,3,4-tetrahydro-2,6-naphthyridine, 2 TFA (0.398 g, 0.908 mmol, 100% yield) as a light-brown oil which crystallized under vacuum. The residue was used in the next step with no additional purification. LC/MS: m/z 211.00 (M+H)+, 0.270 min (method 7). 1H NMR (500 MHz, MeOD) δ ppm 8.66 (d, 1H) 7.74 (d, J=5.49 Hz, 1H) 7.57-7.67 (m, 5H) 4.69 (s, 2H) 3.54 (t, J=6.10 Hz, 2H) 3.11 (t, J=6.10 Hz, 2H).

Workup

  1. customThe mixture was flushed with N2
  2. customwas purged with H2
  3. stirringAfter stirring
  4. customthe reaction for 3 h it
  5. filtrationwas filtered through a pad of CELITE®
  6. concentrationThe organic solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fdbdcee348d442a790aeafeae3bd10c5
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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