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1,10-Phenanthroline → 6-(2-Fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine

HRID 1401111
Notes
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Reaction equation

HRID 1401111 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+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)(O)[O-].[Na+].Cl[C:35]1[N:40]=[CH:39][C:38]2[N:41]=[C:42]([C:44]3[CH:49]=[C:48]([CH3:50])[C:47]([O:51][CH3:52])=[C:46]([CH3:53])[CH:45]=3)[O:43][C:37]=2[CH:36]=1>CN(C)C=O.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:35]1[N:40]=[CH:39][C:38]2[N:41]=[C:42]([C:44]3[CH:45]=[C:46]([CH3:53])[C:47]([O:51][CH3:52])=[C:48]([CH3:50])[CH:49]=3)[O:43][C:37]=2[CH:36]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 13181,10-PhenanthrolineHCID 97072-FluorophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 717431286-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

Product 1

HCID 711865366-(2-Fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine
Yield 10.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

In a microwaveable vessel, 0.65 g of 6-chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine were dissolved in 12 ml of absolute N,N-dimethylformamide, and 0.25 g of 2-fluorophenol, 0.88 g of cesium carbonate, 21 mg of copper (I) iodide and 40 mg of 1,10-phenanthroline were added. In a microwave reactor, the reaction was heated at 200° C. for 1 h. 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 means of preparative HPLC, giving 86 mg (10%) 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 means of preparative HPLC

Sources & evidence

ORD record
ord-c61f3af7c74e466e89ab391eb6be26e2
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08907093B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes