Tetrahydrofuran → HCID 57933080, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57932943	—
Reactant	HCID 178505803	HCID 178505803	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	HCID 57933080	HCID 57933080	46%

Reaction Steps

Using a procedure similar to Example 32, 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.50 g, 1.27 mmol) and PdCl2(dppf) (0.047 g, 0.063 mmol) and 0.5 M solution of 3-fluorophenylzinc iodide in THF (5.1 mL, 2.55 mmol) furnish the title compound (0.24 g, 0.59 mmol, 46%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.76-1.94 (m, 4H), 2.17 (s, 3H), 2.51 (s, 3H), 2.53 (s, 3H), 3.31-3.39 (m, 1H), 6.69 (s, 1H), 6.94-7.01 (m, 1H), 7.26 (s, 1H), 7.30-7.42 (m, 3H). LC/MS (m/z): calcd. for C24H26FN3S (M+H)+: 408.7; found: 408.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-231b47f0c05641208d3be72c54b8487f
Source note	uspto-grants-2009_11