Acrylic Acid → HCID 178525329, compound

HRID 2289974Notes

Reaction equation

HRID 2289974 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[C:25]([OH:29])(=[O:28])[CH:26]=[CH2:27].C(N(CC)CC)C>CN(C=O)C.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](/[CH:27]=[CH:26]/[C:25]([OH:29])=[O:28])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 178522917HCID 178522917, compound

Product 1

HCID 178525329HCID 178525329, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the title compound of Example 5 (0.913 g), acrylic acid (0.17 mL), palladium acetate (4 mg) and triethylamine (0.70 mL) in 5 mL DMF is heated to 100° C. for 24 h in a pressure-safe tube. The reaction is cooled and diluted with 50 mL of a 10% aqueous HCl solution. The resulting solid is collected, dried and recrystallized from EtOH to yield 0.564 g of the desired product as a tan solid.

Workup

  1. temperatureThe reaction is cooled
  2. customThe resulting solid is collected
  3. customdried
  4. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-c954aae83b534c4fa94d18934ce7b61d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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