Methyl Acrylate → HCID 54189349, compound

HRID 659115Notes

Reaction equation

HRID 659115 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.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39](Br)[N:38]=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:39]1[CH:40]=[CH:41][CH:42]=[C:37]([NH2:36])[N:38]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 54189349HCID 54189349, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Tri(o-toly)phosphine (26 mg, 0.086 mmol), palladium(II) acetate (214 mg, 0.96 mmol), methyl acrylate (90 mg, 1.04 mmol), triethylamine (351 mg, 3.47 mmol) and 2-amino-6-bromopyridine (37) (150 mg, 0.87 mmol) in acetonitrile (3 mL) were heated in a CEM Discover microwave for 1 hour at 90° C. The solvent was removed under a stream of nitrogen gas; 4N HCl was added and the aqueous extracted with TBME (×2). The aqueous layer was then basified to pH 9/10 using K2CO3(aq) and extracted with EtOAc (×5). The organic layer was washed with brine, dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was partially purified by column chromatography eluting with 50% EtOAc in heptane to give the title compound. Yield: 95 mg, 61%; LC-MS tr 0.76 min; HPLC Purity: 42%; MS (ES+) m/z 179 (M+H)

Workup

  1. customThe solvent was removed under a stream of nitrogen gas
  2. addition4N HCl was added
  3. extractionthe aqueous extracted with TBME (×2)
  4. extractionextracted with EtOAc (×5)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationthe solvent concentrated in vacuo
  8. customThe crude product was partially purified by column chromatography
  9. washeluting with 50% EtOAc in heptane

Sources & evidence

ORD record
ord-93e149185bbc45849a805c506eb00a54
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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