Tetrahydrofuran → HCID 69007102, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	2-Bromo-6-ethylpyridine	HCID 12954800	—
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	HCID 69007102	HCID 69007102	28.3%

Reaction Steps

Using a procedure similar to Example 31, 2-bromo-6-ethyl pyridine (0.26 g, 1.41 mmol), 1.56 M n-Bu-Li (0.94 mL, 1.47 mmol), 0.5 M ZnCl2 in THF (3.0 mL, 1.53 mmol), 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) (0.047 g, 0.064 mmol) produce the title compound (0.15 g, 0.36 mmol, 28%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.34 (t, J=7.5 Hz, 3H), 1.75-1.94 (m, 4H), 2.16 (s, 3H), 2.51 (s, 3H), 2.52 (s, 3H), 2.85 (q, J=16.2, 7.5 Hz, 2H), 3.31-3.41 (m, 1H), 6.67 (s, 1H), 7.01 (d, J=7.8 Hz, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.53 (s, 1H), 8.59 (t, J=7.8 Hz, 1H). LC/MS (m/z): calcd. for C25H30N4S (M+H)+: 419.3; found: 419.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-bc1b66291cd34f31813941fc307a98ff
Source note	uspto-grants-2009_11