2-Bromo-6-(methylsulfonyl)pyridine → 8-(1-Ethyl-propyl)-3-[5-(6-methanesulfonyl-pyridin-2-yl)-3-methyl-thiophen-2-yl]-2,6-dimethyl-imidazo[1,2-b]pyridazine

Participants

Role	Name	HCID	Charge
Reactant	2-Bromo-6-(methylsulfonyl)pyridine	HCID 13433422	—
Reactant	3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57932943	—
Reactant	Butyllithium	HCID 178418339	—
Catalyst	Zincchloride	HCID 3007855	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	8-(1-Ethyl-propyl)-3-[5-(6-methanesulfonyl-pyridin-2-yl)-3-methyl-thiophen-2-yl]-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57933089	27.5%

Reaction Steps

Using a procedure similar to Example 25, 2-bromo-6-methanesulfonyl-pyridine (0.29 mL, 1.22 mmol), 1.3 M n-Bu-Li (0.82 mL, 1.07 mmol), ZnCl2 (2.14 mL, 1.07 mmol), 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 1.02 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnish the title compound (0.13 g, 0.28 mmol, 27%). 1H NMR (CDCl3), 60.88 (t, J=7.5 Hz, 6H), 1.75-1.93 (m, 4H), 2.18 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 3.30 (s, 3H), 3.30-3.38 (m, 1H), 6.70 (s, 1H), 7.64 (s, 1H), 7.83 (dd, J=7.6, 0.8 Hz, 1H), 7.89 (dd, J=7.9, 0.8 Hz, 1H), 7.93 (dd, J=7.9, 7.6 Hz, 1H). LC/MS (m/z): calcd. for C24H28N4O2S2 (M+H)+: 469.3; found: 469.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-41491503a0b44accada898ef6f736fc7
Source note	uspto-grants-2009_11