Pyrazole → tert-butyl-3-(1H-pyrazol-1-yl)benzylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Pyrazole	HCID 1048	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	tert-Butyl 3-iodobenzylcarbamate	HCID 11645663	—
Reactant	(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine	HCID 13822957	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-butyl-3-(1H-pyrazol-1-yl)benzylcarbamate	HCID 56791985	70.3%

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of tert-butyl-3-iodobenzylcarbamate (550 mg, 1.65 mmol) in Dioxane (1.2 mL) and DMSO (1.2 mL) was added CuI (16 mg, 0.083 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.052 ml, 0.33 mmol), pyrazole (135 mg, 1.98 mmol) and K2CO3 (479 mg, 3.47 mmol). After stirring at 120° C. for 3 h, it was concentrated and the residue was purified by column chromatography to give tert-butyl-3-(1H-pyrazol-1-yl)benzylcarbamate (317 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09102625B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-953510000c43469085ac5217a1dfbbdd
Source note	uspto-grants-2015_08