Sodium Carbonate → Ethyl 3-[6-(2-fluorophenyl)pyridin-3-yl]propanoate

HRID 1896691Notes

Reaction equation

HRID 1896691 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10](Br)=[CH:11][CH:12]=1)[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])=[CH:11][CH:12]=1)[CH3:2]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343542-Fluorophenylboronic acidHCID 86251977Ethyl 3-(6-bromopyridin-3-yl)propanoate

Product 1

HCID 68537058Ethyl 3-[6-(2-fluorophenyl)pyridin-3-yl]propanoate

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1000 mg (3.87 mmol) of 3-(6-bromopyridin-3-yl)propionic acid ethyl ester, 596.3 mg (4.26 mmol) of 2-fluorophenylboronic acid, 43.5 mg (0.19 mmol) of palladium acetate, 101.6 mg (0.38 mmol) of triphenylphosphane, 3.88 ml of a 1M sodium carbonate solution, 23 ml of toluene and 6 ml of ethanol was heated under reflux for 5 h and, after cooling, poured into water. The resulting mixture was extracted with ethyl acetate. The organic phase was separated and concentrated, and the residue was purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 782 mg (74%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. temperatureafter cooling
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. customThe organic phase was separated
  6. concentrationconcentrated
  7. customthe residue was purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-f941f4758891409f8de78a52061d3575
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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