3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine → HCID 57932983, compound

Participants

Role	Name	HCID	Charge
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 57932983	HCID 57932983	68%

Reaction Steps

Using a procedure similar to Example 25 from 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.40 g, 0.1.02 mmol), 1.34 M n-Bu-Li (1.60 mL, 2.14 mmol), 0.5 M ZnCl2 (4.3 mL, 2.14 mmol) and PdCl2(dppf) (0.037 g, 0.051 mmol) furnishes the title compound (0.25 g, 0.69 mmol, 68%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 0.97 (t, J=7.5 Hz, 3H), 1.40-1.51 (m, 2H), 1.67-1.92 (m, 6H), 2.07 (s, 3H), 2.46 (s, 3H), 2.51 (s, 3H), 2.83 (t, J=8.0 Hz, 2H), 3.30-3.38 (m, 1H), 6.64 (s, 1H), 6.70 (s, 1H) LC/MS (m/z): calcd. for C22H31N3S (M+H)+: 370.3; found: 370.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612067B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-e75cb446fa09412aba0f5862eb50f356
Source note	uspto-grants-2009_11