trans-Ethyl 3-(4-cyano-3-fluorophenyl)-2-propenoate → HCID 18536111, compound

HRID 412192Notes

Reaction equation

HRID 412192 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[F:16])#[N:2]>CO.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[F:16])#[N:2]

Participants

4

Reactant 1

HCID 23021829trans-Ethyl 3-(4-cyano-3-fluorophenyl)-2-propenoate

Product 1

HCID 18536111HCID 18536111, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Step B (1.3 g, 5.9 mmol) in 30 mL of methanol was added 10% palladium on carbon (130 mg). The solution was stirred at room temperature under an atmosphere of hydrogen for 2 hours, then purged with argon. The mixture was filtered through celite, the filter pad was washed with methanol, and the filtrate was concentrated in vacuo. The crude product was purified on a C18 preparative HPLC column to give the titled product after conversion to the free base.

Workup

  1. custompurged with argon
  2. filtrationThe mixture was filtered through celite
  3. washthe filter pad was washed with methanol
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude product was purified on a C18 preparative HPLC column

Sources & evidence

ORD record
ord-5c5b2f468a4446d6b5f3a3c1ffad90d1
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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