Tetrahydrofuran → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(3-methyl-3H-imidazol-4-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	5-Iodo-1-methyl-1H-imidazole	HCID 1277668	—
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	8-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(3-methyl-3H-imidazol-4-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine	HCID 57932946	15%

Reaction Steps

Using the procedure analogous to Example 31, 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), 1.34M n-Bu-Li (0.80 mL, 1.07 mmol), 0.5M ZnCl2 in THF (2.14 mL, 1.07 mmol), 5-iodo-1-methyl-1H-imidazole (0.24 g, 1.22 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.061 g, 0.15 mmol, 15%). 1H NMR (CDCl3) δ 0.89 (t, J=7.4 Hz, 6H), 1.75-1.93 (m, 4H), 2.17 (s, 3H), 2.50 (s, 3H), 2.53 (s, 3H), 3.24-3.38 (m, 1H), 3.61 (s, 3H), 6.68 (s, 1H), 7.02 (s, 1H), 7.23 (s, 1H), 7.55 (s, 1H). LC/MS (m/z): calcd. for C22H27N5S (M+H)+: 394.3; found: 394.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-a5c0a62b30fb4d46b357bd62206d1b02
Source note	uspto-grants-2009_11