Water → 6-Chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carbonitrile

https://huagongshe.com/reaction/2203343

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	6-Chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine	HCID 86678978	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ammonium Hydroxide	HCID 14923	—
Product	6-Chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carbonitrile	HCID 86678979	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of the intermediate from Step H (4.32 g, 10.18 mmol) in DMF (50 mL) was added zinc cyanide (2.39 g, 20.35 mmol), Pd2 dba3 (0.47 g, 0.51 mmol), DPPF (0.564 g, 1.02 mmol), and water (2.5 mL). The resulting solution was heated at 120° C. for 18 hours. The reaction was cooled to room temperature, diluted with 15% NH4OH solution (10 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. m/z=323.9 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365574B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-95459e3e17d343bc87e15af7dd127799
Source note	uspto-grants-2016_06