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Hydrochloric Acid → 2-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylcyclopropanecarbonitrile

HRID 218135
Notes
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Reaction equation

HRID 218135 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=NNS(C4C=CC(C)=CC=4)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[C:39](#[N:42])[CH:40]=[CH2:41]>O1CCOCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:41][CH:40]4[C:39]#[N:42])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 86640188N'-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methylene)-4-methylbenzenesulfonohydrazide

Product 1

HCID 592510952-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylcyclopropanecarbonitrileYield 21%

Reagents, catalysts & solvents

2
HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(c)(d) N′-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methylene)-4-methylbenzenesulfonohydrazide (1.82 g, 3.77 mmol) was dissolved in 20 mL of dioxane and 20 mL of a 50% aqueous NaOH solution and heated at 85 C. After 1 h, the reaction mixture was adjusted to pH 4-5 with conc HCl and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated, and the crude product was taken to the next step. Crude residue was dissolved in 20 mL of benzene and acrylonitrile (4 mmol) was added. The reaction mixture was heated to reflux. After 2 h, the reaction was poured into brine and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated, and then purified by HPLC to give 275 mg (21% yield) of 2-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylcyclopropanecarbonitrile. MS found: (M+H)+=354.

Workup

  1. extractionextracted 2× EtOAc
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionCrude residue was dissolved in 20 mL of benzene
  6. temperatureThe reaction mixture was heated to reflux
  7. waitAfter 2 h
  8. extractionextracted 2× EtOAc
  9. dry with materialThe organic layers were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by HPLC

Sources & evidence

ORD record
ord-08bd22541c014e59b08c2ff509e6d74a
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198311B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes