Benzene, 1-chloro-4-fluoro- → 5-allyloxy-N-(4-chlorophenyl)indole

HRID 342767

反応式

HRID 342767 の反応式
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH:4]=[CH2:5].F[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1>O1CCCC1>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2)[CH:4]=[CH2:5]

参加物

5

反応物 3

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 142392305-(prop-2-en-1-yloxy)-1H-indole

生成物 1

HCID 544104885-allyloxy-N-(4-chlorophenyl)indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of sodium hydride (60%, 254 mg, 6.35 mmol) in 15 mL tetrahydrofuran (THF) was added 5-allyloxyindole (Step A; 1.0 g, 5.77 mmol) in 5 mL THF and the mixture was stirred for 1 hour at ambient temperature. 4-fluorochlorobenzene (0.69 mL, 6.35 mmol) was added and the reaction heated to reflux for 21 hours. After cooling, the reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to provide the title compound.

後処理

  1. temperaturethe reaction heated
  2. temperatureto reflux for 21 hours
  3. temperatureAfter cooling
  4. customthe reaction was quenched with saturated aqueous ammonium chloride
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-795c175dcce247b2aacf26afcf06a6ac
出典データセット
uspto-grants-1999_01
特許番号
US05859051

関連ノート

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