HCID 68157042, compound → HCID 68157586, compound

HRID 243257Notes

Reaction equation

HRID 243257 reaction equation
[F:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1>CCOC(C)=O>[F:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:4]([NH:11][CH:12]([CH3:13])[CH3:14])[C:5]([NH2:8])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 68157042HCID 68157042, compound

Product 1

HCID 68157586HCID 68157586, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(3-Fluoro-6-nitro-2-pyridin-2-yl-phenyl)isopropylamine (0.49 g, 1.79 mmol) was dissolved in EtOAc (10 mL). The flask was evacuated and purged with N2. Pd/C (10%) was added and the mixture was hydrogenated at atmospheric pressure under a H2 atmosphere. The mixture was stirred overnight. The flask was evacuated and purged with N2. The catalyst was removed by filtration and the filtrate was concentrated in vacuo and the resulting residue was purified by chromatography (Si—PPC, gradient 0-50% EtOAc/cyclohexane) to afford the title compound as a yellow oil (0.47 g, 99%). 1H NMR (CDCl3, 400 MHz): δ 8.71 (1H, ddd, J=6.6, 2.4, 1.3 Hz), 7.78 (1H, ddd, J=10.6, 10.2, 2.5 Hz), 7.57 (1H, ddt, J=10.6, 5.2, 1.4 Hz), 7.26 (1H, ddd, J=10.0, 6.6, 1.6 Hz), 6.76-6.66 (2H, m), 5.34 (1H, br s), 3.80 (2H, br s), 3.19 (1H, sept, J=8.5 Hz), 7.63 (6H, d, J=8.5 Hz)

Workup

  1. customThe flask was evacuated
  2. custompurged with N2
  3. additionPd/C (10%) was added
  4. customThe flask was evacuated
  5. custompurged with N2
  6. customThe catalyst was removed by filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe resulting residue was purified by chromatography (Si—PPC, gradient 0-50% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-2d50151022ac4a90b5c6ae2d76191166
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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