Potassium Carbonate → HCID 21966481, compound

HRID 2212584Notes

Reaction equation

HRID 2212584 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[CH3:16].[C:17](=[O:20])([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][N:9]([CH3:12])[C:10]1[CH:11]=[CH:2][C:3]([CH:17]=[O:20])=[CH:4][C:5]=1[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])([CH3:14])[CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1[CH3:16]

Participants

8

Reactant 2

HCID 11430Potassium CarbonateHCID 219664297-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one

Product 1

HCID 21966481HCID 21966481, compoundYield 168.7%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-dimethylamino-3-formyl-1-phenyl boronic acid (11.5 g, 59.5 mmol), 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one (Example 1d) (14.0 g, 49.6 mmol) and potassium carbonate (13.7 g, 99.2 mmol) in toluene (140 mL), ethanol (28 mL) and water (21 mL) was degassed with argon for 40 minutes. Tetrakis(triphenylphosphine)palladium(0) (3.5 g, 0.06 mmol) was added and the mixture heated at reflux under argon for 24 hrs. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (30% ethyl acetate in hexane) to give 14.66 g of 4-Dimethylamino-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde (84%). 1H NMR (300 MHz; CDCl3): 1.31 (s, 3 H), 1.33 (s, 3 H), 2.10 (s, 3 H), 2.53 (s, 2 H), 2.69 (s, 6 H), 3.36 (s, 3 H), 6.89 (s, 1 H), 6.99 (d, J=8.7 Hz, 1 H), 7.14 (s, 1 H), 7.58 (d, J=2.4 Hz, 1 H), 7.77 (dd, J=2.4 Hz and 8.4 Hz, 1 H), 9.82 (s, 1 H).

Workup

  1. customwas degassed with argon for 40 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 24 hrs
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-434f808ed99342c086b1bafd43e11d52
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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