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

HRID 570518노트

반응식

HRID 570518 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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-143f6f879a1448ba8fe0902f03a5d181
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023849B2

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