Triethylamine → HCID 24769524, compound

HRID 1625058Notes

Reaction equation

HRID 1625058 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[N:22]=1.[C:28]1([C@@H:34]([NH:36][C:37](=[O:40])[CH:38]=[CH2:39])[CH3:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:27][C:23]1[N:22]=[C:21](/[CH:39]=[CH:38]/[C:37]([NH:36][C@H:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:35])=[O:40])[CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 122742,6-DibromopyridineHCID 11480756N-((S)-1-phenylethyl)acrylamide

Product 1

HCID 24769524HCID 24769524, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To the solution of triphenylphosphine (0.496 mmol) in DMF (10 mL), a palladium acetate (0.245 mmol) was added at room temperature under argon atmosphere. The mixture was stirred for 5 min then 2,6-dibromopyridine (12.7 mmol) followed by N-((S)-1-phenylethyl)acrylamide (14.0 mmol) and triethylamine (35.9 mmol) were added and the reaction mixture was stirred at 140° C. for 7 hr. The majority of the solvent was removed under diminished pressure. Diluted HCl was added and the product was extracted with ethyl acetate. Organic layers were combined, washed with brine, dried over sodium sulfate. Drying agent and solvent was removed and product was purified by column chromatography using hexanes and hexanes:ethyl acetate 2:1 as eluents, to give pure product with a good yield.

Workup

  1. additionwere added
  2. stirringthe reaction mixture was stirred at 140° C. for 7 hr
  3. customThe majority of the solvent was removed under diminished pressure
  4. additionDiluted HCl was added
  5. extractionthe product was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customDrying agent and solvent
  9. customwas removed
  10. customproduct was purified by column chromatography
  11. customto give pure product with a good yield

Sources & evidence

ORD record
ord-f2f4f7b7e9bb4bf38258c06fd9829441
Source dataset
uspto-grants-2014_07
Patent number
US08779151B2

Reaction notes

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