5'-nitro-4-(3-triflouromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl → 4-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-ylamine

HRID 1510261Notes

Reaction equation

HRID 1510261 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[F:25][C:22]([F:23])([F:24])[C:18]1[CH:17]=[C:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][N:8]=3)[CH2:15][CH2:14]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 674357105'-nitro-4-(3-triflouromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl

Product 1

HCID 593712454-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5′-nitro-4-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (500 mg, 1.42 mmol) from above in ethanol (15 mL) was added 10% palladium on carbon (100 mg). The mixture was hydrogenated at 50 psi for 2 hr. The mixture was filtered over celite and the solvents were evaporated to give 4-(3-trifluoromethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-ylamine that was used in the next step with further purification. LCMS calcd for C17H18F3N3 (m/e) 321, obsd 322 (M+H).

Workup

  1. filtrationThe mixture was filtered over celite
  2. customthe solvents were evaporated

Sources & evidence

ORD record
ord-128f02ee908a4a35b59a34215d54f29a
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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