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

HRID 242034Notes

Reaction equation

HRID 242034 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:25])=[C:7]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[O:15])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1.[CH3:26][N:27](CCN(C)C)C.CCOC(C)=O.CCCCCC>CN(C=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:26]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:25])=[C:7]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[O:15])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1)#[N:27]

Participants

8

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 21226206Ethyl acetate hexaneHCID 56847017HCID 56847017, compound

Product 1

HCID 56847076HCID 56847076, compoundYield 118.2%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

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]+.

Workup

  1. customflushed with nitrogen three times
  2. temperatureAfter cooling to RT the mixture
  3. filtrationwas filtered through celite
  4. washwas washed with dichloromethane
  5. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-0acc900060ba4bb8af04051bac350c34
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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