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

HRID 1401111Notes

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

Participants

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

extractionextracted three times with ethyl acetate
washThe combined organic phases were washed with saturated aqueous sodium bisulaite solution
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
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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