Tetrahydrofuran → HCID 57933081, 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 178424429	HCID 178424429	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	HCID 57933081	HCID 57933081	46%

Reaction Steps

Using the procedure analogous to Example 32, 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.15 g, 0.38 mmol) and PdCl2(dppf) (0.014 g, 0.019 mmol) and 0.5M solution of 2-methylphenylzinc iodide in THF (3 mL, 1.53 mmol) furnish the title compound (0.069 g, 0.17 mmol, 46%). 1H NMR (CDCl3) δ 0.90 (t, J=7.5 Hz, 6H), 1.76-1.94 (m, 4H), 2.19 (s, 3H), 2.53 (s, 3H), 2.54 (s, 3H), 2.55 (s, 3H), 3.32-3.40 (m, 1H), 6.68 (s, 1H), 7.02 (s, 1H), 7.22-7.30 (m, 3H), 7.48-7.53 (m, 1H). LC/MS (m/z): calcd. for C25H29N3S (M+H)+: 404.3; found: 404.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-24dad7d28dd54c5e8a9fded44760fe28
Source note	uspto-grants-2009_11