Quinoline → 4-[2-(4-Fluorophenyl)thiophen-3-yl]pyridine

HRID 9880

Reaction equation

N1C2C(=CC=CC=2)C=CC=1.C([C:14]1[S:18][C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:16]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH:15]=1)(O)=O>[Cu]>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[S:18][CH:14]=[CH:15][C:16]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 240 °C

Procedure

Quinoline (42 ml) and copper powder (2.95 g, 46.4 mmol) were added to 5-carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (12.64 g (42.2 mmol), prepared as described in 2))), and the resulting mixture was stirred at 240° C. for 2.5 hours. At the end of this time, the reaction mixture was cooled to room temperature and was filtered off. The filtrate was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=1:1), to give the title compound (11.81 g) as a brown powder (yield quantitative).

Workup

temperatureAt the end of this time, the reaction mixture was cooled to room temperature
filtrationwas filtered off
customThe filtrate was partitioned between ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed by distillation under reduced pressure
customThe residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-a6d16c84992d44c5ba2388e74f39994d
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091352B2

Linked notes

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