HCID 90403013, compound → HCID 90403525, compound

HRID 1049376Notes

Reaction equation

HRID 1049376 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:4]=[C:3]1[CH3:23]>CO.[Pd]>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[N:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:4]=[C:3]1[CH3:23]

Participants

4

Reactant 1

HCID 90403013HCID 90403013, compound

Product 1

HCID 90403525HCID 90403525, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(1,2-dimethyl-1H-imidazol-5-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (0.08 g, 0.257 mmol) in MeOH (20 mL) was treated with 10% Pd/C (50% w/w water, 2.73 mg, 0.001 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed with warm MeOH and the filtrate concentrated to dryness to afford 5-((2-(1,2-dimethyl-1H-imidazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (50 mg, 69%). 1H NMR (400 MHz, DMSO-d6): δ 8.41 (d, J=5.8 Hz, 1H), 7.81 (d, J=2.9 Hz, 1H), 7.29 (dd, J=8.9, 3.0 Hz, 1H), 7.23 (s, 1H), 7.13 (d, J=2.4 Hz, 1H), 6.66 (dd, J=5.7, 2.5 Hz, 1H), 6.51 (d, J=8.9 Hz, 1H), 6.02 (s, 2H), 3.80 (s, 3H), 2.32 (s, 3H); MS (ESI) m/z: 282.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-a6cc4ec560d744bcae211de8cc8b4aa5
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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