Methyl Acrylate → 3-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid methyl ester

HRID 659112

Reaction equation

HRID 659112 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C.Br[C:37]1[CH:38]=[C:39]([C:43]2[O:44][C:45]3[CH:51]=[CH:50][C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[CH:48][C:46]=3[N:47]=2)[CH:40]=[CH:41][CH:42]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:28][O:27][C:23](=[O:26])[CH:24]=[CH:25][C:41]1[CH:42]=[CH:37][CH:38]=[C:39]([C:43]2[O:44][C:45]3[CH:51]=[CH:50][C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[CH:48][C:46]=3[N:47]=2)[CH:40]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 593348442-(3-Bromo-phenyl)-5-phenyl-benzoxazole

Product 1

HCID 684169753-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Tri(o-toly)phosphine (9 mg, 0.030 mmol), palladium(II) acetate (6 mg, 0.027 mmol), methyl acrylate (31 mg, 0.34 mmol), triethylamine (116 mg, 1.14 mmol) and aryl bromide (32) (100 mg, 0.29 mmol) in acetonitrile (3 mL) were heated in a CEM Discover microwave for 90 minutes at 90° C. The solvent was removed under a stream of nitrogen gas, water was added and the organics extracted with EtOAc. The organic layer was dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 20% EtOAc in heptane. Yield: 41 mg, 40%; LC-MS tr 1.86 min; HPLC Purity: 67%; MS (ES+) m/z 356 (M+H)

Workup

  1. customThe solvent was removed under a stream of nitrogen gas, water
  2. additionwas added
  3. extractionthe organics extracted with EtOAc
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationthe solvent concentrated in vacuo
  6. customThe crude product was purified by column chromatography
  7. washeluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-21798cf6470c46bf8402031b875a3969
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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