HCID 90403425, compound → HCID 90403203, compound

HRID 1049349Notes

Reaction equation

HRID 1049349 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[O:21]1[C:17]([C:13]2[CH:12]=[C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[N:9][CH:8]=3)[CH:16]=[CH:15][N:14]=2)=[CH:18][N:19]=[CH:20]1

Participants

4

Reactant 1

HCID 90403425HCID 90403425, compound

Product 1

HCID 90403203HCID 90403203, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)oxazole (0.092 g, 0.324 mmol) in MeOH (10 mL) was treated with 10% Pd/C (50% wet, 0.034 g, 0.032 mmol) and hydrogenated (1 atm) for 5 h. The solid was removed via filtration through diatomaceous earth and the filtrate concentrated to dryness to afford 5-((2-(oxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (73 mg, 89%). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (s, 1H), 8.46 (d, J=5.7 Hz, 1H), 7.84 (d, J=2.9 Hz, 1H), 7.76 (s, 1H), 7.32 (dd, J=8.9, 3.0 Hz, 1H), 7.15 (d, J=2.5 Hz, 1H), 6.86 (dd, J=5.7, 2.5 Hz, 1H), 6.53 (d, J=8.9 Hz, 1H), 6.06 (s, 2H); MS (ESI) m/z: 255.1 (M+H+).

Workup

  1. customThe solid was removed via filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-b3de3ad80f5a4a209ec9c840c8870bb3
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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