Triethylamine → HCID 14851309, compound

HRID 1029464Notes

Reaction equation

HRID 1029464 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].CCN(CC)CC.Br[C:16]1[C:17]([CH:34]([CH3:36])[CH3:35])=[N:18][N:19]([C:28]2[CH:33]=[N:32][CH:31]=[CH:30][N:29]=2)[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[N:19]([C:28]3[CH:33]=[N:32][CH:31]=[CH:30][N:29]=3)[N:18]=[C:17]([CH:34]([CH3:36])[CH3:35])[C:16]=2/[CH:3]=[CH:2]/[C:1]([O:5][CH2:6][CH3:7])=[O:4])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl Acrylate2×HCID 14851308HCID 14851308, compound

Product 1

HCID 14851309HCID 14851309, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Bis(triphenylphosphine) palladium (II) chloride (2.55 g, 3.6 mmol) and ethyl acrylate (49.2 mL, 454 mmol) were dissolved in DMF (200 mL) and Et3N (200 mL) at reflux under an inert atmosphere. The bromopyrazole (32.82 g, 91 mmol, Step B) was then added and the reaction was refluxed overnight. An additional 0.005 eq of catalyst and 10 mL of ethyl acrylate were added to push the reaction to completion. The reaction was cooled and partitioned between H2O and EtOAc. The organic layer was dried (MgSO4) and evaporated to give a brown oil. Elution from a 6-inch silica column gave 20.3 g (59%) of a tan solid. Recrystallization from hexanes produced a brilliant white solid.

Workup

  1. temperaturethe reaction was refluxed overnight
  2. customthe reaction to completion
  3. temperatureThe reaction was cooled
  4. custompartitioned between H2O and EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customto give a brown oil
  8. washElution from a 6-inch silica column

Sources & evidence

ORD record
ord-7116e22cf4bf4f618518a73b611cca88
Source dataset
uspto-grants-1992_04
Patent number
US05102893

Reaction notes

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