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

HRID 9880

반응식

HRID 9880 반응식
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

참가 물질

4

반응물 2

HCID 7047QuinolineHCID 219885025-Carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene

생성물 1

HCID 219884884-[2-(4-Fluorophenyl)thiophen-3-yl]pyridine수율 109.6%

시약·촉매·용매 1

HCID 23978Copper촉매

반응 조건

온도
240 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a6d16c84992d44c5ba2388e74f39994d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091352B2

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