Methyl Acrylate → HCID 59526490, compound

HRID 1880608Notes

Reaction equation

HRID 1880608 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].I[C:8]1[C:9]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1N2CCN(CC2)C1>[N:18]1([C:9]2[C:8](/[CH:3]=[CH:2]/[C:1]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=[C:11]([C:14]([F:17])([F:15])[F:16])[N:10]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 59526479HCID 59526479, compound

Product 1

HCID 59526490HCID 59526490, compoundYield 94.5%

Reagents, catalysts & solvents 3

HCID 9237DabcoCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

70 μl (1.0 mmol) methyl acrylate was added to a mixture of 237 mg (0.66 mmol) 3-iodo-2-(piperidin-1-yl)-6-(trifluoromethyl)pyridine, 3 mg (0.01 mmol) Pd(OAc)2, 2.2 mg (0.02 mmol) DABCO and 91 mg (0.66 mmol) K2CO3 in 3 ml DMF under a nitrogen atmosphere. The reaction mixture was stirred in a sealed tube at 80° C. for 24 h. The mixture was cooled to RT, filtered through celite with EtOAc eluation. The organic phase was washed with water, dried and concentrated. Flash chromatography (SiO2, Pet. Ether/EtOAc 8/1) afforded 196 mg (94%) of the title compound.

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered through celite with EtOAc eluation
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c28933afa304423a5b99e9564dc755f
Source dataset
uspto-grants-2012_11
Patent number
US08318768B2

Reaction notes

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