N,N,N',N'-Tetramethylethylenediamine → HCID 56847076, compound

https://huagongshe.com/reaction/242034

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	Ethyl acetate hexane	HCID 21226206	—
Reactant	HCID 56847017	HCID 56847017	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 56847076	HCID 56847076	118.2%

Reaction Conditions

Temperature	160 °C

Reaction Steps

To a solution of 247 mg (0.61 mmol) 7-bromo-N-[(3-fluorophenyl)-methyl]-1,4-dimethyl-2-oxo-1H-quinoline-3-carboxylic acid amide (example 16) in DMF (3 mL) were added 20 μL (0.22 mmol) TMEDA, 43 mg (0.37 mmol) Zinccyanide, 1 mg (0.003 mmol) Pd2 dba3 and 7 mg (0.019 mmol) Xantphos. The reaction solution was degasses and flushed with nitrogen three times and then heated in MW to 160° C. for 4 min. After cooling to RT the mixture was filtered through celite and was washed with dichloromethane. The combined filtrates were concentrated in vacuo. After CC (EtOAc/hexane 1:2) of the residue, 91 mg (0.26 mmol, 43%) 7-cyano-N-[(3-fluorophenyl)-methyl]-1,4-dimethyl-2-oxo-1H-quinoline-3-carboxylic acid amide (example 20) were obtained. MS: m/z 350.1 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08653102B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-0acc900060ba4bb8af04051bac350c34
Source note	uspto-grants-2014_02