2-(1-Methyl-1h-imidazol-4-yl)-4-[(6-nitro-3-pyridinyl)oxy]pyridine → 5-((2-(1-methyl-1H-imidazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine

HRID 2278911Notes

Reaction equation

HRID 2278911 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([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)[N:4]=[CH:3]1>CO.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([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)[N:4]=[CH:3]1

Participants

4

Reactant 1

HCID 904032142-(1-Methyl-1h-imidazol-4-yl)-4-[(6-nitro-3-pyridinyl)oxy]pyridine

Product 1

HCID 904032995-((2-(1-methyl-1H-imidazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(1-methyl-1H-imidazol-4-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (1.61 g, 5.42 mmol) in MeOH (30 mL) was treated with 10% Pd/C (50% w/w water, 0.576 g, 0.542 mmol) and hydrogenated (50 psi) overnight. The solids were removed via filtration through diatomaceous earth, washed with warm MeOH and the filtrate was concentrated to dryness to afford 5-((2-(1-methyl-1H-imidazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (1.311 g, 91%). 1H NMR (400 MHz, DMSO-d6): δ 8.31 (d, J=5.7 Hz, 1 H), 7.81 (d, J=2.9 Hz, 1 H), 7.65 (d, J=1.3 Hz, 1 H), 7.58 (s, 1 H), 7.29 (dd, J=8.9, 3.0 Hz, 1 H), 7.19 (d, J=2.6 Hz, 1 H), 6.73 (dd, J=5.7, 2.6 Hz, 1 H), 6.52 (d, J=8.9 Hz, 1 H), 6.03 (s, 2 H), 3.67 (s, 3 H); MS (ESI) m/z: 268.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-fc158c8d3c344f75ab1538469e327c20
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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