Water → HCID 66742761, compound

HRID 449572Notes

Reaction equation

HRID 449572 reaction equation
Br.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13](=[O:18])[C:14](Br)([CH3:16])[CH3:15])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C.C(OCC)(=O)C>[CH2:10]([O:12][C:13](=[O:18])[C:14]([O:9][C:6]1[CH:7]=[N:8][C:3]([NH2:2])=[CH:4][CH:5]=1)([CH3:16])[CH3:15])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 667434106-Aminopyridin-3-ol--hydrogen bromide (1/1)

Product 1

HCID 66742761HCID 66742761, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 6-aminopyridin-3-ol hydrobromide (2 g, 10.5 mmol) and ethyl-2-bromo-2-methylpropanate (2.04 g, 10.5 mmol) in anhydrous acetonitrile (25 ml) was added cesium carbonate (10.7 g, 33 mmol) and the material was stirred for 16 hours under argon atmosphere. Water (60 ml) and ethyl acetate (60 ml) were added and the material was shaken in a reparatory funnel. The organic phase was collected and the aqueous phase was back extracted with ethyl acetate (2×50 ml). The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. to provide a golden brown solid (1.626 g)(M+H)+=225 m/e.

Workup

  1. stirringthe material was shaken in a reparatory funnel
  2. customThe organic phase was collected
  3. extractionthe aqueous phase was back extracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d17ffcd18b84499082bb828e3ddafced
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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