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Dichloromethane → 1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazole-3-carbonitrile

HRID 1482921
Notes
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Reaction equation

HRID 1482921 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]#[N:10])=[N:2]1.Br[CH2:12][C:13]1[C:18]([F:19])=[CH:17][C:16]([O:20][CH2:21][CH3:22])=[CH:15][C:14]=1[F:23].C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>CN(C=O)C.O>[CH2:21]([O:20][C:16]1[CH:15]=[C:14]([F:23])[C:13]([CH2:12][N:1]2[C:5]3[CH2:6][CH2:7][CH2:8][C:4]=3[C:3]([C:9]#[N:10])=[N:2]2)=[C:18]([F:19])[CH:17]=1)[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 231351391H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrileHCID 467376162-(Bromomethyl)-5-ethoxy-1,3-difluorobenzene

Product 1

HCID 900127051-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

3.40 g of 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonitrile (CAS-RN 851776-29-9) (25.5 mmol, 1.00 eq) were dissolved in 35 mL dry DMF under nitrogen atmosphere. 7.05 g 2-(bromomethyl)-5-ethoxy-1,3-difluorobenzene (28.1 mmol, 1.10 eq.) and 9.98 g cesiumcarbonate (30.1 mmol, 1.20 eq.) were added and stirred over night at rt. DCM and water were added, the aqueous phase was washed twice with DCM, the organic phase was washed with brine and was dried with magnesiumsulfate, was concentrated in vacuo and purified by flash chromatography (hexane/tert-butyl methyl ether-gradient with hexane 100-70%) to provide 1.07 g (3.45 mmol, 14%) of the analytically pure target compound.

Workup

  1. washthe aqueous phase was washed twice with DCM
  2. washthe organic phase was washed with brine
  3. dry with materialwas dried with magnesiumsulfate
  4. concentrationwas concentrated in vacuo
  5. custompurified by flash chromatography (hexane/tert-butyl methyl ether-gradient with hexane 100-70%)
  6. customto provide 1.07 g (3.45 mmol, 14%) of the analytically pure target compound

Sources & evidence

ORD record
ord-13f86f4d6dc347db98e0f2365f215484
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09416125B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes