HCID 67359927, compound → HCID 59280055, compound

HRID 1518148Notes

Reaction equation

HRID 1518148 reaction equation
[N+:1]([C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[N:5]=1)([O-])=O>CCO.[Pd]>[F:20][C:17]([F:18])([F:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:6]1[N:5]=[C:4]([NH2:1])[C:9]([NH2:10])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 67359927HCID 67359927, compound

Product 1

HCID 59280055HCID 59280055, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-3-ylamine (130 mg, 0.460 mmol, as prepared in the previous step) in EtOH (10 mL), 10% Pd/C (60 mg) was added. The resulting mixture was hydrogenated at 50 psi for 3 h. The reaction mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to obtain the title compound, which was directly used in the next step without further purification. 1H-NMR (400 MHz, CDCl3) δ: 7.62 (d, J=7.8 Hz, 1H), 7.41-7.49 (m, 1H), 7.29-7.41 (m, 2H), 6.81 (d, J=7.8 Hz, 1H), 6.64 (d, J=7.8 Hz, 1H), 4.31 (br. s., 2H), 3.34 (br. s., 2H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5fdf45d633764983b446718876022bd1
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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