Ethanol → 3-(3-Chloro-4-pyridin-3-yl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine, hydrochloride salt

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	3-Iodopyridine	HCID 70714	—
Reactant	3-(4-Bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57933078	—
Catalyst	Zinc	HCID 23994	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	Hydrochloric Acid	HCID 313	—
Product	3-(3-Chloro-4-pyridin-3-yl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine, hydrochloride salt	HCID 131727721	52.6%

Reaction Steps

Using a procedure analogous to Example 175, 3-(4-bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 0.97 mmol), Reike® Zn (0.5 g/mL solution in THF, 2.5 mL, 1.94 mmol), 3-iodo-pyridine (0.30 g, 1.45 mmol), PdCl2(dppf) (0.035 g, 0.048 mmol), and a 1 M solution of HCl in EtOH (0.61 mL, 0.61 mmol) furnish the title compound (0.076 g, 0.17 mmol, 18%). 1H-NMR (CDCl3), δ 0.95 (t, J=7.0 Hz, 6H), 1.71-1.88 (m, 2H), 1.88-2.01 (m, 2H), 2.68 (s, 3H), 2.81 (s, 3H), 3.85-3.96 (m, 1H), 5.28 (s, 1H), 7.27 (bs, 1H), 8.09 (bs, 1H), 8.23 (bs, 1H), 8.70 (bs, 1H), 8.89 (bs, 1H), 9.18 (bs, 1H). LC/MS (m/z): calcd. for C22H24Cl2N4S (M+H)+: 411.1; found: 411.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-d88e559ad38b44f581c3388f929f217f
Source note	uspto-grants-2009_11