Triethylamine → N-tert-butyl-6-(5-((3-fluoropyridine-2-yl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Fluoro-2-iodopyridine	HCID 1519483	—
Reactant	N-tert-butyl-6-(5-ethynylthiophene-2-yl)imidazo[2,1-b]thiazole-5-amine	HCID 86625957	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Product	N-tert-butyl-6-(5-((3-fluoropyridine-2-yl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amine	HCID 24876138	77.2%

Reaction Steps

A solution of 450 mg (1.49 mmol) N-tert-butyl-6-(5-ethynylthiophene-2-yl)imidazo[2,1-b]thiazole-5-amine, 333 mg (1.90 mmol) 3-fluoro-2-iodo-pyridine, 38 mg (0.06 mmol) bis(triphenylphosphine)-palladium-(II)-chloride, 19 mg (0.07 mmol) copper-(I)-iodide and 389 μl (2.80 mmol) NEt3 in AE (21 ml) was heated to 50° C. while being stirred for 20 h. Concentration in a vacuum was subsequently performed and a CC (AE) carried out with the residue, whereby 456 mg (1.15 mmol, 77%) N-tert-butyl-6-(5-((3-fluoropyridine-2-yl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amine was obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07893069B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-c7152efbdece49cfad64e5844e2a6359
Source note	uspto-grants-2011_02