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

HRID 1361118Notes

Reaction equation

HRID 1361118 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[C:7]=1/[CH:8]=[N:9]/[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.[Cl-].[NH4+].[Cu]I>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:9]=[CH:8][C:7]=12

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 59278325N-[(E)-(3,5-dibromo-4-pyridinyl)methylideneamino]-4-fluoroaniline

Product 1

HCID 592784604-Bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-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-(3,5-dibromopyridin-4-yl)-meth-(E)-ylidene]-N′-(4-fluorophenyl)-hydrazine (2.0 g, 5.4 mmol), CuI (50.0 mg, 0.260 mmol), trans-N,N′-dimethylcyuclohexane-1,2-diamine (0.200 mL, 1.27 mmol), and K2CO3 (1.4 g, 0.010 mol) in NMP (10 mL) was warmed at 120° C. for 30 minutes. The reaction was monitored by HPLC-MS indicating the desired mass. The mixture was diluted with aqueous ammonium chloride (100 mL) and the resulting solid collected by filtration. The solid was dissolved in hot ethyl acetate (EtOAc), dried over magnesium sulfate, treated with activated carbon, filtered through diatomaceous earth and concentrated. The residue was passed through a pad of silica gel eluting with dichloromethane to afford 4-bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine.

Workup

  1. filtrationthe resulting solid collected by filtration
  2. dissolutionThe solid was dissolved in hot ethyl acetate (EtOAc)
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with activated carbon
  5. filtrationfiltered through diatomaceous earth
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c73be6178ad47e59579dba6e3aeb066
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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