HCID 68751051, compound → HCID 68746979, compound

HRID 333331Notes

Reaction equation

HRID 333331 reaction equation
[C:1](/[C:3](=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]>CC(O)=O.[Zn]>[C:1]([CH:3]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:16][CH:17]=1)[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])#[N:2]

Participants

4

Reactant 1

HCID 68751051HCID 68751051, compound

Product 1

HCID 68746979HCID 68746979, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (Z)-tert-butyl 2-cyano-3-(4-(pyridin-2-yl)phenyl)acrylate (340 mg, 1.110 mmol) and zinc (1089 mg, 16.65 mmol) in AcOH (6.5 ml) was stirred at 100° C. for 2 hours. The mixture was cooled to room temperature and filtered. To the filtrate was added EtOAc and water, and the mixture was basified by aq. NaOH. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 15 to 30% EtOAc/Heptane) and gave the title compound: 150 mg (yield: 44%). LCMS (condition B): 309.2 (M+1); retention time=1.09 min.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionTo the filtrate was added EtOAc and water
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by flash chromatography (silica gel, 15 to 30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-f5202b5ba9f64577952218278c9eab8b
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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