6-Nitro-1H-indole → 1-(3,5-difluoro-benzyl)-6-nitro-1H-indole

HRID 1158829ノート

反応式

HRID 1158829 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=1>CN(C)C=O>[F:21][C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([F:22])[CH:18]=1)[CH2:14][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[CH:9]1

参加物

4

反応物 2

HCID 785026-Nitro-1H-indoleHCID 5188963,5-Difluorobenzyl bromide

生成物 1

HCID 667754591-(3,5-difluoro-benzyl)-6-nitro-1H-indole収率 123.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

—Sodium hydride (50% dispersion in oil, 4.8 g, 100 mmol) was added to a solution of 6-nitroindole (15.0 g, 92.6 mmol) in dry dimethylformamide (750 ml). After 30 min. stirring, 1-bromomethyl-3,5-difluoro-benzene (19.5 g, 94 mmol) was added. Stirring was continued for 1 h and the reaction mixture was quenched with water. The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was stirred with heptane to produce a white solid which was collected by filtration to give 1-(3,5-difluoro-benzyl)-6-nitro-1H-indole (33 g). The product was used in the following step without further purification.

後処理

  1. stirringStirring
  2. waitwas continued for 1 h
  3. customthe reaction mixture was quenched with water
  4. extractionThe product was extracted into ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. stirringThe crude product was stirred with heptane
  9. customto produce a white solid which
  10. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-4159bac931194365819048bf141834fb
出典データセット
uspto-grants-2010_10
特許番号
US07812036B2

反応ノート

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