Triethylamine → 2-[4-[4-Hydroxybut-1-ynyl]phenyl]-7-methylimidazo[1,2-a]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Butyn-1-OL	HCID 13566	—
Reactant	2-(4-Bromophenyl)-7-methylimidazo[1,2-a]pyridine	HCID 717644	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Acetonitrile	HCID 6342	—
Product	2-[4-[4-Hydroxybut-1-ynyl]phenyl]-7-methylimidazo[1,2-a]pyridine	HCID 22015594	71.7%

Reaction Conditions

Temperature	60 °C

Reaction Steps

The product of Step A (1.8 g) in dry acetonitrile (40 mL) was treated sequentially with tetrakis(triphenylphosphine)palladium(0) (0.1 g), triethylamine (1.27 g), and CuI (10 mg) then heated at 60° C. for 30 minutes. The mixture was cooled to ambient temperature, treated with 3-butyn-1-ol (0.361 g) and heated at reflux temperature for 18 hours. The mixture was cooled to ambient temperature and evaporated to dryness. The residue was crystallized, twice, from acetone to afford the title compound (1.02 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07041828B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-c06b31c63e984abc83389f5125a7bc3f
Source note	uspto-grants-2006_05