Dimethylformamide → 4-Bromo-1-(oxan-4-yl)-1H-pyrazole

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate	HCID 13961807	—
Reactant	4-Bromo-2H-1,2,3-triazole	HCID 178419468	—
Solvent	Water	HCID 962	—
Product	4-Bromo-1-(oxan-4-yl)-1H-pyrazole	HCID 51063926	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 4-bromo-triazole (0.30 g), toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester (0.52 g), cesium carbonate (1.00 g), and N,N-dimethylformamide (7 mL) was stirred at 60° C. overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was triturated with cyclohexane/diethyl ether to afford the title compound as a colorless solid. Yield: 0.26 g (55% of theory); LC (method 3): tR=2.75 min; Mass spectrum (ESI+): m/z=231/233 (Br) [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09090605B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-bd6fd05487e849b89bd75222eaaee6c7
Source note	uspto-grants-2015_07