HCID 15477227, compound → HCID 15477206, compound

HRID 366319Notes

Reaction equation

C([C:4]1[O:5][C:6]2[C:12]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])=[C:11]([F:26])[CH:10]=[C:9]([Cl:27])[C:7]=2[CH:8]=1)(O)=O>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Cl:27][C:9]1[C:7]2[CH:8]=[CH:4][O:5][C:6]=2[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[C:11]([F:26])[CH:10]=1

Participants

Conditions

Temperature: 200 °C

Procedure

7.0 g (17 mmol) of 3-(2-carboxy-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 5.0 g (79 mmol) of copper powder, were suspended in 50 ml of quinoline, followed by stirring at 200° C. for 1 hour. After completion of the reaction, the reaction solution was subjected to filtration. The filtrate was extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution and water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography, to obtain 3.5 g (yield: 56%) of the desired product as white crystals. Melting point: 127-128° C.

Workup

customAfter completion of the reaction
filtrationthe reaction solution was subjected to filtration
extractionThe filtrate was extracted with ethyl acetate
washThe organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution and water
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a3f60688849049b189d903b748d98948
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

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