Cesium carbonate → 1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonitrile

HRID 536486ノート

反応式

HRID 536486 の反応式
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]#[N:10])=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C=O)C>[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][N:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]#[N:10])=[N:2]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 231351391H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrile

生成物 1

HCID 712853771-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

10.320 g (77.50 mmol) of 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonitrile was dissolved in 100 ml DMF, 30.304 g (93.01 mmol) of caesium carbonate and 16.116 g (85.26 mmol) of 2-fluorobenzyl bromide were added and it was stirred at RT overnight. The reaction mixture was concentrated by evaporation and taken up in dichloromethane and water was added. The organic phase was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, filtered on a silicone filter and concentrated by evaporation. The residue was purified by silica-gel flash chromatography (eluent: hexane/ethyl acetate, gradient). 11.37 g (60% of theor.) of the target compound was obtained.

後処理

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. additionwater was added
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. filtrationfiltered on a silicone
  7. filtrationfilter
  8. concentrationconcentrated by evaporation
  9. customThe residue was purified by silica-gel flash chromatography (eluent: hexane/ethyl acetate, gradient)
  10. custom11.37 g (60% of theor.) of the target compound was obtained

出典と根拠

ORDレコード
ord-03b9d815b3e743ea8922af16125b6382
出典データセット
uspto-grants-2014_10
特許番号
US08859569B2

反応ノート

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