2-Bromopropane → 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine

Participants

Role	Name	HCID	Charge
Reactant	2-Bromopropane	HCID 6358	—
Reactant	Sodium Azide	HCID 33557	—
Reactant	5-Bromo-3-ethynylpyridin-2-amine	HCID 45789786	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	2-Methylpropan-2-ol--water (1/1)	HCID 71401949	—
Product	5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine	HCID 90273155	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of isopropyl bromide (5.0 g, 40.65 mmol) and sodium azide (2.6 g, 40.65 mmol) in t-BuOH/water (1:2) (50 mL) was stirred for 2 h at 80° C. Then the reaction mixture was cooled to room temperature, to which was added 5-bromo-3-ethynyl-pyridin-2-ylamine (0.8 g, 4.065 mmol) and CuI (catalytic amount). The reaction mixture was stirred for 16 h at 80° C. The reaction mixture was cooled to RT, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford crude compound. Crude compound was washed with diethyl ether to afford the title compound as ash colour solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09393248B1
Source dataset	uspto-grants-2016_07
ORD ID	ord-fd4c640655444d879826f6a5b57a6d48
Source note	uspto-grants-2016_07