N,N,N',N'-Tetramethylethylenediamine → HCID 56848134, compound

https://huagongshe.com/reaction/2093727

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	Cyclohexane ethylacetate	HCID 21867204	—
Reactant	7-Bromo-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide	HCID 56848080	—
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 56848134	HCID 56848134	191.5%

Reaction Conditions

Temperature	160 °C

Reaction Steps

To a solution of 880 mg (2.13 mmol) 7-Bromo-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 28) in DMF (3 mL) were added 70 μL (0.47 mmol) TMEDA, 152 mg (1.28 mmol) Zinccyanide, 4 mg (0.007 mmol) Pd2 dba3 and 25 mg (0.040 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 it was washed with dichloromethane. The combined organic layers were concentrated in vacuo. After CC (EtOAc/cyclohexane 1:2) of the residue, 325 mg (0.90 mmol, 42%) 7-Cyano-2-cyclopropyl-N-[(4-fluorophenyl)-methyl]-4-methyl-quinoline-3-carboxylic acid amide (example 38) were obtained. MS: m/z 360.1 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08445512B2
Source dataset	uspto-grants-2013_05
ORD ID	ord-78188a9e4d9f41d0b380faacf1ed9dde
Source note	uspto-grants-2013_05