Hydrochloric Acid → 6-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

HRID 1401110Notes

Reaction equation

N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[C:23]1[CH:28]=[C:27]([Cl:29])[N:26]=[CH:25][C:24]=1[NH:30][C:31](=[O:42])[C:32]1[CH:37]=[C:36]([CH3:38])[C:35]([O:39][CH3:40])=[C:34]([CH3:41])[CH:33]=1>O1CCCC1.[Cu]I>[Cl:29][C:27]1[N:26]=[CH:25][C:24]2[N:30]=[C:31]([C:32]3[CH:37]=[C:36]([CH3:38])[C:35]([O:39][CH3:40])=[C:34]([CH3:41])[CH:33]=3)[O:42][C:23]=2[CH:28]=1

Participants

Conditions

Temperature: 180 °C

Procedure

In a microwaveable vessel, 0.98 g of N-(4,6-dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamide were dissolved in 15 ml of dry tetrahydrofuran, and 29 mg of copper(I) iodide, 54 mg of 1,10-phenanthroline and 1.47 g of cesium carbonate were added. In a microwave sunthesizer, the reaction mixture was then heated at 180° C. for 3 h. For work-up, the mixture was added to 12 ml of a 0.5 M aqueous hydrochloric acid solution. The precipitated solid was filtered off with suction and the mother liquor was extracted twice with ethyl acetate. The collected organic phases were combined with the suction-filtered solid and the solvent was removed under reduced pressure. This gave 0.79 g (91%) of the product, which was reacted further without any further purification.

Workup

filtrationThe precipitated solid was filtered off with suction
extractionthe mother liquor was extracted twice with ethyl acetate
customthe solvent was removed under reduced pressure
customThis gave 0.79 g (91%) of the product, which was reacted further without any further purification

Sources & evidence

ORD record: ord-2419ef62c3e9457e8cefa041ff8bd9bf
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907093B2

Reaction notes

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