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 2278911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278911
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fc158c8d3c344f75ab1538469e327c20
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133183B2

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