Triethylamine → HCID 13369430, compound

HRID 1049454Notes

Reaction equation

HRID 1049454 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:8][C:4]1[CH:3]=[C:2](/[CH:11]=[CH:10]/[C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:6][N:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 13369430HCID 13369430, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, to a solution of 4-bromo-2-methylpyridine (1.78 mL) in DMF (35 mL) were added ethyl acrylate (8.13 mL), palladium (II) acetate (168 mg), tri-o-tolylphosphine (685 mg) and triethylamine (6.27 mL), and the mixture was stirred at 100° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-957f2ad97cf9415bacbe9fe20401e53d
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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