HCID 90403801, compound → HCID 90403322, compound

HRID 1049268Notes

Reaction equation

HRID 1049268 reaction equation
[CH:1]([C:4]1[NH:5][C:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:17]=[N:18][C:19]([N+:22]([O-])=O)=[CH:20][CH:21]=3)[CH:12]=[CH:11][N:10]=2)=[CH:7][N:8]=1)([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([C:4]1[NH:5][C:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[N:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:7][N:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 90403801HCID 90403801, compound

Product 1

HCID 90403322HCID 90403322, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(2-isopropyl-1H-imidazol-5-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (612 mg, 1.881 mmol) and 10% Pd/C (50% wet, 200 mg, 0.188 mmol) in MeOH (10 mL) was hydrogenated (1 atm) for 24 h. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness to afford 5-((2-(2-isopropyl-1H-imidazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (529 mg, 95%). 1H NMR (400 MHz, DMSO-d6): δ 11.96 (s, 1H), 8.30 (d, J=5.6 Hz, 1H), 7.81 (d, J=2.9 Hz, 1H), 7.51 (s, 1H), 7.29 (dd, J=8.9, 3.0 Hz, 1H), 7.20 (d, J=2.5 Hz, 1H), 6.67 (dd, J=5.7, 2.5 Hz, 1H), 6.52 (d, J=8.9 Hz, 1H), 6.03 (s, 2H), 2.97 (m, 1H), 1.21 (d, J=7.0 Hz, 6H); MS (ESI) m/z: 296.1 (M+H+).

Workup

  1. customfor 24 h
  2. customThe solids were removed via filtration through diatomaceous earth
  3. washwashed with MeOH
  4. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-76f1e3d8b9614a13a03efa9213f134d0
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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