Potassium Carbonate → HCID 86696383, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Carboxyphenylboronic Acid	HCID 312183	—
Reactant	3-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine	HCID 86696322	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Acetonitrile--water (1/1)	HCID 18373917	—
Product	HCID 86696383	HCID 86696383	226.6%

Reaction Conditions

Temperature	145 °C

Reaction Steps

To the mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (340 mg, 1.26 mmol), 4-boronobenzoic acid (210 mg, 1.26 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (44 mg, 0.063 mmol) and potassium carbonate (261 mg, 1.89 mmol) was added 3:1 acetonitrile/water (3 mL). The resulting mixture was heated at 145° C. (microwave) for 800 s. The reaction was then filtered and concentrated to afford 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoic acid (886 mg, >100% yield) as a crude off-white solid: LRMS (ESI) m/e 311.2 [(M+H)+, calcd for C17H19N4O2 311.2].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08969565B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-c88469973ca845369bdb86212189180a
Source note	uspto-grants-2015_03