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

HRID 9880

反応式

HRID 9880 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 23978Copper触媒

反応条件

温度
240 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a6d16c84992d44c5ba2388e74f39994d
出典データセット
uspto-grants-2006_08
特許番号
US07091352B2

関連ノート

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