Sodium Carbonate → HCID 71534385, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Cyanophenylboronic acid	HCID 2734325	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine	HCID 71534384	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	HCID 71534385	HCID 71534385	52%

Reaction Steps

To a solution of 6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (500 mg, 1.52 mmol) and 3-cyanophenylboronic acid (336 mg, 2.29 mmol) in dioxane/H2O (10 mL/2 mL) was added Na2CO3 (322 mg, 3.04 mmol) followed by Pd(dba)2 (175 mg, 0.30 mmol) and X-Phos (73 mg, 0.15 mmol) under nitrogen with stirring. The mixture was stirred at reflux for 15 h under nitrogen. After cooling, the solvent was concentrated in vacuo. The residue was purified by chromatography (silica, ethyl acetate) to give 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzonitrile (310 mg, 52%) as a yellow oil. LC-MS: 396.2 [M+H]+, tR=1.89 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09169259B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-d06e472cd3cf443a8bfaedac83a65b9f
Source note	uspto-grants-2015_10