Tetrahydrofuran → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-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 178426002	HCID 178426002	—
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-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine	HCID 57932953	47%

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 (0.60 g, 1.53 mmol) and PdCl2(dppf) (0.056 g, 0.076 mmol) and 0.5 M solution of 6-methyl-2-pyridylzinc bromide in THF (6.0 mL, 3.06 mmol) furnish the title compound (0.29 g, 0.72 mmol, 47%). 1H NMR (CDCl3), δ 0.89 (t, J=7.5 Hz, 6H), 1.73-1.93 (m, 4H), 2.16 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 2.58 (s, 3H), 3.31-3.40 (m, 1H), 6.67 (s, 1H), 7.00 (d, J=7.9 Hz, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.52 (s, 1H), 8.56 (t, J=7.7 Hz, 1H). LC/MS (m/z): calcd. for C24H28N4 (M+H)+: 405.7; found: 405.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-bc4f8dcda318460e83a3d69740841413
Source note	uspto-grants-2009_11