2-Bromothiazole → 3-(3-Chloro-4-thiazol-2-yl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Participants

Role	Name	HCID	Charge
Reactant	2-Bromothiazole	HCID 76430	—
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	3-(3-Chloro-4-thiazol-2-yl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57933061	47.5%

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 (0.25 g, 0.61 mmol), Reike® Zn (0.5 g/mL solution in THF, 1.6 mL, 1.21 mmol), 2-bromo-thiazole (0.11 mL, 1.21 mmol), and PdCl2(dppf) (0.022 g, 0.030 mmol) furnish the title compound (0.012 g, 0.29 mmol, 6.8%). 1H-NMR (CDCl3), δ 0.89 (t, J=7.5 Hz, 6H), 1.75-1.94 (m, 4H), 2.52 (s, 6H), 3.27-3.43 (m, 1H), 6.73 (s, 1H), 7.43 (d, J=3.3 Hz, 1H), 7.94 (d, J=3.3 Hz, 1H), 8.30 (s, 1H) ppm. LC/MS (m/z): calcd. for C20H21ClN4S2 (M+H)+: 417.1; found: 417.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-137837eb0e19460d87e9d1ed0118d956
Source note	uspto-grants-2009_11