Methyl Acrylate → HCID 53762108, compound

HRID 1084344Notes

Reaction equation

HRID 1084344 reaction equation
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:21][O:20][C:16]([CH:17]=[CH:18][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)=[O:19]

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 14256374HCID 14256374, compound

Product 1

HCID 53762108HCID 53762108, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

500 mg of dimethyl 5-bromo-pyridine-2,4-dicarboxylate (from Example 3) are heated at 140° C. in an autoclave with 10 ml of methyl acrylate, 0.5 ml of triethylamine, 11 mg of palladium diacetate and 22 mg of triphenylphosphine for 14 hours. After cooling, the mixture is diluted with ethyl acetate, the solid is filtered off and the solvent is evaporated together with the excess methyl acrylate. The product is chromatographed (silica gel) to give 330 mg of a white solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off
  3. customthe solvent is evaporated together with the excess methyl acrylate
  4. customThe product is chromatographed (silica gel)

Sources & evidence

ORD record
ord-8ec55d3446ac47079cdc0b6b37f3c259
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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