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

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	3-Bromo-1-methyl-1H-pyrazole	HCID 14948637	—
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-(1-methyl-1H-pyrazol-3-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine	HCID 57933040	10%

Reaction Steps

Using a 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), 1.42 M n-Bu-Li (0.75 mL, 1.07 mmol), 0.5 M ZnCl2 in THF (2.14 mL, 1.07 mmol), 3-bromo-1-methyl-1H-pyrazole (Pavlik, J.; Kurzweil, E.; J. Org. Chem., 1991, 56, 22, 6313) (0.20 g, 1.22 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.041 g, 0.10 mmol, 10%). 1H NMR (CDCl3) δ 0.90 (t, J=7.5 Hz, 6H), 1.75-1.94 (m, 4H), 2.15 (s, 3H), 2.51 (s, 3H), 2.52 (s, 3H), 3.31-3.41 (m, 1H), 3.95 (s, 3H), 6.47 (d, J=2.2 Hz, 1H), 6.67 (s, 1H), 7.25 (s, 1H), 7.36 (d, J=2.2 Hz, 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-98bd2af0dc294317a7a843aceb891330
Source note	uspto-grants-2009_11