3,6-Dichloropyridazine → 6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-chloro-pyridazine

Participants

Role	Name	HCID	Charge
Reactant	3,6-Dichloropyridazine	HCID 67331	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	9-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine	HCID 58299585	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-chloro-pyridazine	HCID 58299683	97%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of compound 4 (1.50 g, 5.92 mmol), 3,6-dichloropyridazine (0.882 g, 5.92 mmol), bis(dibenzylideneacetone)palladium (0.170 g, 0.296 mmol), Xantphos (0.514 g, 0.888 mmol) and sodium tert-butoxide (0.854, 8.88 mmol) in toluene (80 mL) was purged with nitrogen. The reaction was then heated at 100° C. for one hour in a sealed vessel. After cooling to room temperature, the mixture was loaded onto a silica gel column and eluted with 2-10% methanol/DCM. Evaporation of combined fractions provided compound 140 (2.1 g) as a yellowish solid. LCMS-ESI, M+1: 366.1

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841312B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-99dcd0086e284629ac36e9e5d3bd5370
Source note	uspto-grants-2014_09