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

HRID 570518ノート

反応式

HRID 570518 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 were dissolved in 100 ml of DMF, 30.304 g (93.01 mmol) of caesium carbonate and 16.116 g (85.26 mmol) of 2-fluorobenzyl bromide were added, and the mixture was stirred at RT overnight. The mixture was concentrated and taken up in dichloromethane, and water was added. The organic phase was removed and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, filtered through a silicone filter and concentrated. The residue was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate, gradient). 11.37 g (60% of theory) of the target compound were obtained.

後処理

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

出典と根拠

ORDレコード
ord-143f6f879a1448ba8fe0902f03a5d181
出典データセット
uspto-grants-2015_05
特許番号
US09023849B2

反応ノート

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