N,N,N',N'-Tetramethylethylenediamine → HCID 56848439, compound

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Ethyl acetate hexane	HCID 21226206	—
Reactant	HCID 56848435	HCID 56848435	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 56848439	HCID 56848439	265.6%

Reaction Conditions

Temperature	160 °C

Reaction Steps

To a solution of 600 mg (1.44 mmol) 7-bromo-2-ethoxy-N-[(3-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 32) in DMF (3 mL) were added 46 μL (0.32 mmol) TMEDA, 102 mg (0.86 mmol) zinc cyanide, 2 mg (0.007 mmol) Pd2 dba3 and 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 it was washed with dichloromethane. The combined organic layers were concentrated in vacuo. After CC (EtOAc/hexane 1:2) of the residue, 310 mg (0.85 mmol, 59%) 7-Cyano-2-ethoxy-N-[(3-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 36) were obtained. MS: m/z 364.1 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08653101B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-5964d46da2ed490d8abd81c8b704ca08
Source note	uspto-grants-2014_02