Triethylamine → 3-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-acrylic acid ethyl ester

HRID 1931417Notes

Reaction equation

HRID 1931417 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.Br[C:31]1[CH:32]=[CH:33][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])=[N:35][CH:36]=1.[CH2:44]([O:46][C:47](=[O:50])[CH:48]=[CH2:49])[CH3:45]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:44]([O:46][C:47](=[O:50])[CH:48]=[CH:49][C:31]1[CH:36]=[N:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])=[CH:33][CH:32]=1)[CH3:45]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 497585155-Bromo-2-(2-fluorophenyl)pyridine

Product 1

HCID 685379763-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
125 °C

Procedure

Under nitrogen, 0.755 g (3.38 mmol) of palladium acetate, 2.05 g (6.75 mmol) of tri(ortho-tolyl)phosphine and 97.8 ml (0.708 mol) of triethylamine were added to a solution of 34.0 g (0.135 mol) of 5-bromo-2-(2-fluoro-phenyl) -pyridine in 2.2 l of acetonitrile. Then 23.38 ml (0.216 mol) of acrylic acid ethyl ester were added, and the mixture was shaken in an autoclave at 125° C. for 20 h. After cooling, the mixture was poured onto ice/water, the mixture stirred at 5 to 10° C. for 1 h, and the precipitated product was collected by filtration and purified by chromatography (silica gel, n-heptane/ethyl acetate 3:1). Yield: 24.3 g.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto ice/water
  3. stirringthe mixture stirred at 5 to 10° C. for 1 h
  4. filtrationthe precipitated product was collected by filtration
  5. custompurified by chromatography (silica gel, n-heptane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-d4540cb3c4f74c22be87813a9cda5ba6
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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