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

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	N-[(E)-(4-bromo-3-pyridinyl)methylideneamino]-4-fluoroaniline	HCID 59278491	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Solvent	Ammonium Chloride	HCID 25517	—
Product	1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine	HCID 59278357	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08063065B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-75ed35f5560b4712922d6cbde3da3afb
Source note	uspto-grants-2011_11