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

HRID 1698121Notes

Reaction equation

HRID 1698121 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.CN[C@@H]1CCCC[C@H]1NC.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

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 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′-dimethylcyclohexane-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-c83f0b25088f4542ab56de6c124a1ec4
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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