Potassium Carbonate → 4-(8-amino-3-(4-hydroxy-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide	HCID 71222797	—
Reactant	4-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol	HCID 71226780	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	4-(8-amino-3-(4-hydroxy-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide	HCID 76901228	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

The reaction mixture of 4-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (580 mg, 1.6 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (2 mmol), Pd(dppf)Cl2 (80 mg) and K2CO3 (830 mg, 6 mmol) in a mixed solvent of dioxane (15 mL) and H2O (2 mL) was stirred at 110° C. for 1.5 hrs under N2 protection. After cooling, the resulting mixture was filtered and the filtrate was evaporated under reduce pressure to dryness. The residue was purified by preparative TLC to afford 4-(8-amino-3-(4-hydroxy-1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09446130B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-835e4eb0a1434566be9252a875d3df25
Source note	uspto-grants-2016_09