Tetrahydrofuran → HCID 57932921, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Chloropyrazine	HCID 73277	—
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 57932921	HCID 57932921	48%

Reaction Steps

Using a procedure similar 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) (example Rupp-2), 2-chloropyrazine (0.11 mL, 1.22 mmol), 1.42 M n-Bu-Li (1.52 mL, 1.07 mmol), 0.5 M ZnCl2 in THF (2.14 mL, 1.07 mmol), and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.19 g, 0.49 mmol, 48%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.75-1.94 (m, 4H), 2.20 (s, 3H), 2.52 (s, 3H), 2.53 (s, 3H), 3.31-3.40 (m, 1H), 6.69 (s, 1H), 7.63 (s, 1H), 8.40 (d, J=2.6 Hz, 1H), 8.51 (t, J=1.9 Hz, 1H), 8.96 (d, J=0.9 Hz, 1H). LC/MS (m/z): calcd. for C22H25N5S (M+H)+: 392.3; found: 392.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-5f8b317a62c74ada84d549f983fbc7a0
Source note	uspto-grants-2009_11