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

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 178506617	HCID 178506617	—
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-phenyl-thiophen-2-yl)-imidazo[1,2-b]pyridazine	HCID 57932958	50%

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) (0.05 g, 0.069 mmol) and 0.5 M solution of phenylzinc iodide in THF (5.5 mL, 2.76 mmol) furnish the title compound (0.25 g, 0.64 mmol, 50%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.76-1.94 (m, 4H), 2.17 (s, 3H), 2.52 (s, 3H), 2.53 (s, 3H), 3.31-3.41 (m, 1H), 6.68 (s, 1H), 7.26 (s, 1H), 7.27-30 (m, 1H), 7.35-7.41 (m, 2H), 7.61-7.66 (m, 2H). LC/MS (m/z): calcd. for C24H27N3S (M+H)+: 390.3; found: 390.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-169522005e3f45a68d311be35f62151e
Source note	uspto-grants-2009_11