Dimethylformamide → HCID 51050345, compound

HRID 1986499Notes

Reaction equation

HRID 1986499 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:16]#[N:17])=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.[CH:25]([CH:27]=[CH2:28])=[O:26].C(N(CC)CC)C.CN(C)C=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:12]([C:7]1[C:6]([C:16]#[N:17])=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:28]=[CH:27]/[CH:25]=[O:26])[CH:3]=2)[N:8]=1)[CH:13]([CH3:14])[CH3:15]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7847Acrolein2×HCID 8471TriethylamineHCID 51050239HCID 51050239, compound

Product 1

HCID 51050345HCID 51050345, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 167845palladium(II) acetateCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-bromo-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (5.00 g, 13.2 mmol), acrolein (2.22 g, 39.6 mmol), benzyltriethylammonium chloride (3.00 g, 13.2 mmol), triethylamine (5.5 ml, 39.6 mmol), palladium acetate (150 mg, 0.66 mmol) and N,N-dimethylformamide (40 ml) was stirred under an argon atmosphere at 70° C. After 3 hrs., palladium acetate (150 mg, 0.66 mmol) and acrolein (2.22 g, 39.6 mmol) were added to the reaction mixture and the mixture was stirred at the same temperature for 17 hrs. The reaction mixture was diluted with ethyl acetate, washed 4 times with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 2-isobutyl-4-(4-methylphenyl)-6-[(1E)-3-oxoprop-1-en-1-yl]quinoline-3-carbonitrile (3.26 g, yield 70%) as white crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 17 hrs
  2. washwashed 4 times with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b779852038d4c57818a023700003de4
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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