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

HRID 536486노트

반응식

HRID 536486 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-03b9d815b3e743ea8922af16125b6382
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859569B2

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