HCID 15457194, compound → HCID 18408351, compound

HRID 1385952Notes

Reaction equation

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

Participants

Conditions

Temperature: 210 °C

Procedure

0.29 g (0.74 mmol) of 3-(2-carboxy-7-chloro-5-fluorobenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 15 ml of quinoline, and 0.05 g (0.75 mmol) of copper powder was added thereto, followed by stirring at 210° C. for 15 minutes. Then, copper was removed by filtration, and the filtrate was poured into water and acidified by an addition of hydrochloric acid, and then extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.18 g (yield: 70%) of the desired product. Melting point: 178-179° C. 1H-NMR (300 MHz, CDCl3) δ value: 3.74(3H,s), 6.66(1H,d), 6.81(1H,d), 7.20(1H,d), 7.56(1H,d), 7.72(1H,d)ppm.

Workup

customThen, copper was removed by filtration
additionthe filtrate was poured into water
additionacidified by an addition of hydrochloric acid
extractionextracted with ethyl acetate
washAfter washing with water
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationEthyl acetate was distilled off under reduced pressure
customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-7a87ad0c3b58486494737334342eb2b5
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265349B1

Reaction notes

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