2-Chloro-6-(trifluoromethyl)pyridine → HCID 57933091, compound

Participants

Role	Name	HCID	Charge
Reactant	2-Chloro-6-(trifluoromethyl)pyridine	HCID 602334	—
Reactant	3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57932943	—
Reactant	Butyllithium	HCID 178418339	—
Catalyst	Zincchloride	HCID 3007855	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	HCID 57933091	HCID 57933091	43.1%

Reaction Steps

Using a procedure similar to Example 25, 2-chloro-6-trifluoromethyl-pyridine (0.29 mL, 1.22 mmol), 1.34 M n-Bu-Li (0.80 mL, 1.07 mmol), ZnCl2 (2.14 mL, 1.07 mmol), 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 1.02 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.20 g, 0.44 mmol, 43%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.76-1.94 (m, 4H), 2.18 (s, 3H), 2.51 (s, 3H), 2.53 (s, 3H), 3.30-3.40 (m, 1H), 6.69 (s, 1H), 7.50 (dd, J=7.5, 0.9 Hz, 1H), 7.65 (s, 1H), 7.78 (d, J=7.9 Hz, 1H), 7.84 (dd, J=7.9, 7.5 Hz, 1H). LC/MS (m/z): calcd. for C24H25F3N4S (M+H)+: 459.3. found: 459.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-9cb35e1dfd414dde8b1e054cc02d9ba8
Source note	uspto-grants-2009_11