Potassium Carbonate → 4-Bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-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)-(3,5-dibromo-4-pyridinyl)methylideneamino]-4-fluoroaniline	HCID 59278325	—
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	4-Bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine	HCID 59278460	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163918B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-c83f0b25088f4542ab56de6c124a1ec4
Source note	uspto-grants-2012_04