HCID 90426625, compound → HCID 90426318, compound

HRID 2279014Notes

Reaction equation

HRID 2279014 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[S:20][C:19]([CH3:21])=[N:18][CH:17]=3)[CH:11]=2)=[CH:7][CH:6]=[C:5]([N+:22]([O-])=O)[N:4]=1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[N:4]=[C:5]([NH2:22])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[S:20][C:19]([CH3:21])=[N:18][CH:17]=2)[CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 90426625HCID 90426625, compound

Product 1

HCID 90426318HCID 90426318, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(4-((2-ethyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)-2-methylthiazole (756 mg, 2.208 mmol) and 10% Pd/C (50% w/w with water, 235 mg, 0.221 mmol) in MeOH (15 mL) was hydrogenated (1 atm) at RT overnight, then warmed to 50° C. for 4 h. The mixture was cooled to RT, the solids removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness to afford 6-ethyl-5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (79 mg, 11%). MS (ESI) m/z: 313.1 (M+H+).

Workup

  1. customat RT
  2. customovernight
  3. temperatureThe mixture was cooled to RT
  4. customthe solids removed via filtration through diatomaceous earth
  5. washwashed with MeOH
  6. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-831647d2ad8645429368c4e407bbc527
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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