Pyrazole → 4-Pyridinecarboxylic acid, 2-(1H-pyrazol-1-yl)-, methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Pyrazole	HCID 1048	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	2-Bromo-isonicotinic acid methyl ester	HCID 3847768	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	4-Pyridinecarboxylic acid, 2-(1H-pyrazol-1-yl)-, methyl ester	HCID 69083269	—

Reaction Steps

A mixture of commercially available methyl 2-bromoisonicotinate (500 mg; 2.31 mmol), 1H-pyrazole (157 mg; 2.31 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (67 mg; 0.46 mmol), K2CO3 (685 mg; 4.86 mmol), and CuI (22 mg; 0.11 mmol) in anh. toluene (8 ml) was heated at reflux for 16 h. After cooling to rt, water was added, and the mixture was extracted with AcOEt. The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded methyl 2-(1H-pyrazol-1-yl)isonicotinate as an off-white solid. LC-MS (conditions A): tR=0.67 min.; [M+H]+: 204.04 g/mol.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09242970B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-fe7b9d883a184bb49983791d1120547f
Source note	uspto-grants-2016_01