Potassium Carbonate → 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

HRID 2212606

Reaction equation

HRID 2212606 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:21])=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=2)[C:5]([CH3:23])([CH3:22])[CH2:4][C:3]1=[O:24].Br[C:26]1[C:27]([F:37])=[C:28]([CH:31]=[C:32]([F:36])[C:33]=1[O:34][CH3:35])[CH:29]=[O:30].C(=O)([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>[F:37][C:27]1[C:26]([C:9]2[CH:10]=[C:11]3[C:6]([C:5]([CH3:22])([CH3:23])[CH2:4][C:3](=[O:24])[N:2]3[CH3:1])=[CH:7][C:8]=2[CH3:21])=[C:33]([O:34][CH3:35])[C:32]([F:36])=[CH:31][C:28]=1[CH:29]=[O:30]

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 219664313-Bromo-2,5-difluoro-4-methoxybenzaldehydeHCID 21966467HCID 21966467, compound

Product 1

HCID 219664662,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

Reagents, catalysts & solvents 5

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

Procedure

A mixture of 1,4,4,6-tetramethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinoline-2-one (0.36 g, 1.1 mmol), 3-bromo-2,5-difluoro-4-methoxybenzaldehyde (example 13 a) (0.25 g, 0.1 mmol) and potassium carbonate (0.275 g, 1.99 mmol) in toluene (5 mL), ethanol (1 mL) and water (0.75 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) was added and the mixture heated at reflux under argon for 20 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 (0%–20% ethyl acetate in hexane) to give 97 mg of 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde.

Workup

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 20 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 (0%–20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d2d5e6a394c041c89ee0859a93a0cc5d
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Linked notes

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