Methyl Acrylate → 3-[3-(6-Phenyl-pyridin-2-ylsulfanyl)-phenyl]-acrylic acid methyl ester

HRID 659101Notes

Reaction equation

HRID 659101 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:26][O:25][C:21](=[O:24])[CH:22]=[CH:23][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphine2×HCID 593348472-(3-Bromo-phenylsulfanyl)-6-phenyl-pyridine

Product 1

HCID 684127523-[3-(6-Phenyl-pyridin-2-ylsulfanyl)-phenyl]-acrylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst3×HCID 6342AcetonitrileSolvent

Procedure

Crude aryl bromide (14) (100 mg, 0.18 mmol), methyl acrylate (18 mg, 0.21 mmol), triethylamine (71 mg, 0.70 mmol), tri(o-toly)phosphine (5 mg, 0.016 mmol) and palladium(II) acetate (12 mg, 0.054 mmol) in acetonitrile (2 mL) was heated in a CEM Discover microwave for 45 minutes at 90° C. More tri(o-toly)phosphine (3 mg) and palladium(II) acetate (3 mg) were added and the reaction mixture retreated in the microwave for 20 minutes; palladium(II) acetate (2 mg) was then added and the process repeated for a further 25 minutes. The solvent was removed under a stream of nitrogen gas, water was added, and the organics extracted with EtOAc, washed with water, dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was partially purified by column chromatography. Yield: 51 mg, 60%; LC-MS tr 1.82 min; HPLC Purity: 70%; MS (ES+) m/z 348 (M+H)

Workup

  1. waitthe process repeated for a further 25 minutes
  2. customThe solvent was removed under a stream of nitrogen gas, water
  3. additionwas added
  4. extractionthe organics extracted with EtOAc
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationthe solvent concentrated in vacuo
  8. customThe crude product was partially purified by column chromatography
  9. waitLC-MS tr 1.82 min

Sources & evidence

ORD record
ord-4b51303daae144bc97befaa8753a559d
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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