Potassium Carbonate → 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine

HRID 1698156Notes

Reaction equation

HRID 1698156 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1/[CH:8]=[N:9]/[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.[Cl-].[NH4+].[Cu]I>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[CH:8]=[N:9]2)=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 59278491N-[(E)-(4-bromo-3-pyridinyl)methylideneamino]-4-fluoroaniline

Product 1

HCID 592783571-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-[1-(4-bromopyridin-3-yl)-meth-(E)-ylidene]-N′-(4-fluorophenyl)-hydrazine (3.0 g, 0.010 mol), CuI (97 mg, 0.51 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (595 μL, 3.77 mmol), and K2CO3 (2.8 g, 0.020 mol) in NMP (100 mL) was warmed at 120° C. After stifling overnight, the mixture was diluted with aqueous ammonium chloride (400 mL) and the resulting solid collected by filtration. The solid was dissolved in EtOAc, and the aqueous layer was extracted with EtOAc. The combined organics layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography to afford 1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine as an orange solid.

Workup

  1. filtrationthe resulting solid collected by filtration
  2. dissolutionThe solid was dissolved in EtOAc
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organics layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-64100580966041b4aa1e84b4d68c1ced
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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