2-Fluorophenol → HCID 71186579, compound

HRID 2039762Notes

Reaction equation

HRID 2039762 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+].Cl[C:21]1[N:26]=[C:25]2[O:27][C:28]([C:30]3[CH:35]=[C:34]([CH3:36])[C:33]([O:37][CH3:38])=[C:32]([CH3:39])[CH:31]=3)=[N:29][C:24]2=[CH:23][CH:22]=1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:21]1[N:26]=[C:25]2[O:27][C:28]([C:30]3[CH:35]=[C:34]([CH3:36])[C:33]([O:37][CH3:38])=[C:32]([CH3:39])[CH:31]=3)=[N:29][C:24]2=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 97072-FluorophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 71743116HCID 71743116, compound

Product 1

HCID 71186579HCID 71186579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

In a microwaveable vessel, 0.75 g of 5-chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[5,4-b]pyridine were dissolved in 12 ml of absolute N,N-dimethylformamide, and 0.30 g of 2-fluorophenol and 1.02 g of cesium carbonate were added. In a microwave reactor, the reaction was heated at 180° C. for 45 min. For work-up, the mixture was added to saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium bisulaite solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by precipitation from acetonitrile, giving, from solid and mother liquor, a total of 0.52 g (55%) of product.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium bisulaite solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by precipitation from acetonitrile
  7. customgiving, from solid and mother liquor

Sources & evidence

ORD record
ord-8e1b2ee4212c47aba6073bd8ba07e346
Source dataset
uspto-grants-2013_11
Patent number
US08580816B2

Reaction notes

Loading…