HCID 90403164, compound → HCID 90403026, compound

HRID 1049371Notes

Reaction equation

HRID 1049371 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[S:21][CH:20]=[N:19][CH:18]=3)[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.CO.[Pd]>[S: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

5

Reactant 1

HCID 90403164HCID 90403164, compound

Product 1

HCID 90403026HCID 90403026, compoundYield 92.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (0.18 g, 0.599 mmol) in EtOAc (10 mL) and MeOH (3 mL) was treated with 10% Pd/C (50% wet, 0.064 g, 0.060 mmol) and hydrogenated (1 atm) for 16 h. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate was concentrated to dryness to afford 5-((2-(thiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (150 mg, 74%). MS (ESI) m/z: 271.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-c907a96971c94ce7971fcf2e3bd16f02
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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