Sodium Carbonate → Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate

HRID 238299Notes

Reaction equation

HRID 238299 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9](Br)=[CH:10][CH:11]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2856454-Fluorophenylboronic acidHCID 714275823-(6-Bromopyridin-3-yl)acrylic acid methyl ester

Product 1

HCID 68821839Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2980 mg (12.31 mmol) of 3-(6-bromopyridin-3-yl)acrylic acid methyl ester, 2067 mg (14.77 mmol) of 4-fluorophenylboronic acid, 138.2 mg (0.61 mmol) of palladium(II)acetate, 322.9 mg (1.23 mmol) of triphenylphosphane and 14.7 ml of a 1M sodium carbonate solution in 73 ml of toluene and 20 ml of ethanol was heated under reflux for 1.5 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The organic phases were evaporated and residue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 2.4 g (76%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. temperatureAfter cooling
  4. additionthe mixture was poured onto water
  5. extractionextracted with ethyl acetate
  6. customThe organic phases were evaporated
  7. customresidue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-be80b9617cb04a7f8fb3a2c9e0a8cdd0
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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