Hexane → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-trifluoromethyl-thieno[3,2-b]pyridin-2-yl)-imidazo[1,2-b]pyridazine

Participants

Role	Name	HCID	Charge
Reactant	Hexane	HCID 8058	—
Reactant	Dimethylformamide toluene	HCID 21735183	—
Reactant	3-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine	HCID 57752639	—
Reactant	HCID 178526070	HCID 178526070	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-trifluoromethyl-thieno[3,2-b]pyridin-2-yl)-imidazo[1,2-b]pyridazine	HCID 57752697	—

Reaction Conditions

Temperature	210 °C

Reaction Steps

90 mg of 3-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.21 mmol), 57 mg of CF3CO2Na (0.42 mmol) and 80 mg of CuI (0.42 mmol) are placed into microwave vessel with 3 ml of DMF/toluene=2/1. The vial is capped and heated at 210° C. for 60 min in microwave. The reaction mixture is applied onto silica-gel column (Hexane:AcOEt=8:1) directly to produce the tile compound. 27 mg (31%) mass spectrum (m/e): 419 (M+1); 1H-NMR (CDCl3): 8.88 (dd, 1H, J=4.9 Hz, 1.4 Hz), 8.22 (dd, 1H, J=7.8 Hz, 1.4 Hz), 7.4 (dd, 1H, J=7.8 Hz, 4.9 Hz), 6.74 (s, 1H), 3.31 (m, 1H), 2.53 (s, 3H), 2.79 (s, 3H), 1.85 (m, 4H), 0.88 (t, 6H, J=7.4 Hz).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07557103B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-3ed179e965c64c70a68c00dceafd2c28
Source note	uspto-grants-2009_07