Pyrazole → 6-Methyl-3-(1H-pyrazol-1-yl)picolinonitrile

Participants

Role	Name	HCID	Charge
Reactant	Pyrazole	HCID 1048	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine	HCID 13822957	—
Reactant	3-Bromo-6-methylpyridine-2-carbonitrile	HCID 21952747	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	6-Methyl-3-(1H-pyrazol-1-yl)picolinonitrile	HCID 117728152	64%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 3-bromo-6-methylpicolinonitrile (1 g, 5.1 mmol), 1H-pyrazole (0.52 ml, 7.61 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.97 ml, 6.09 mmol), Cs2CO3 (2.48 g, 7.61 mmol) and CuI (97 mg, 0.51 mmol) in DMF (10 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a yellow oil (600 mg, 64%). MS (ESI) 185 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440982B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-3f695cb7893047ccbf9393b06ea224d3
Source note	uspto-grants-2016_09