Sodium Carbonate → Ethyl 6-(4-methylphenyl)-2-pyridineacrylate

HRID 1277276Notes

Reaction equation

HRID 1277276 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:4][CH:3]=1.B([O-])([O-])O[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[Cl-].[Na+].O.O.C(OCC)(=O)C>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]2[N:7]=[C:6]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:4][CH:3]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 54398507HCID 54398507, compoundHCID 866453334-Methylphenyl borate2×

Product 1

HCID 53950625Ethyl 6-(4-methylphenyl)-2-pyridineacrylateYield 93%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

In 1,2-dimethoxyethane (4 ml) were dissolved ethyl 6-bromo-2-pyridineacrylate (512 mg, 2.00 mmol) and 4-methylphenyl borate (299 mg, 2.20 mmol), and to the mixture were added sodium carbonate (424 mg, 4.00 mmol), water (2 ml) and tetrakis-(triphenylphosphine)palladium (116 mg, 0.10 mmol). The mixture was stirred at 80° C. for 10 hours. To complete the reaction, 4-tolyl borate (150 mg, 1.10 mmol) and tetrakis(triphenyl-phosphine)palladium (116 mg, 0.10 mmol) were added at 80° C. to the mixture, and the mixture was stirred for 14 hours. To the mixture was added ethyl acetate (30 ml), and the mixture was water (5 ml×2) and saturated brine (5 ml). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 15 g, ethyl acetate/hexane=1/19), and the desired fraction was concentrated under reduced pressure to give ethyl 6-(4-methylphenyl)-2-pyridineacrylate (495 mg, 1.85 mmol, 93%).

Workup

  1. additionwere added at 80° C. to the mixture
  2. stirringthe mixture was stirred for 14 hours
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with column chromatography (silica gel 15 g, ethyl acetate/hexane=1/19)
  6. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf556220d63c48099b8ecbe10953e6b9
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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