Potassium Carbonate → HCID 77231256, compound

HRID 1519549Notes

Reaction equation

HRID 1519549 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7](F)[C:6]=1[Cl:14].[C:16](=O)([O-])[O-:17].[K+].[K+]>CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]([O:17][CH3:16])[C:6]=1[Cl:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86694462HCID 86694462, compound

Product 1

HCID 77231256HCID 77231256, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A solution of methyl(2-chloro-4-cyano-3-fluorophenyl)acetate (1.40 g, 6.2 mmol) from example XX, Step B, was divided into 2 reactions in 2×20 mL Micro Wave (MW) vials, potassium carbonate (0.85 g, 6.2 mmol each vial) and MeOH (15 mL each vial) were added. Each reaction was heated at 130° C. for 60 minutes. The reactions were combined and concentrated, the residue was diluted with water, acidified with 2M HCl and extracted 2× with ethyl acetate, and the organic layers were washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was taken up in 1:1 MeOH:DCM (40 mL) and excess 2M trimethylsilyldiazomethane in ether was added until the yellow color persisted, the excess was quenched with acetic acid and the solution was concentrated in vacuo. Flash chromatography (40% DCM/hexanes to 100% DCM) gave the title ester. 1H-NMR (500 MHz, CDCl3) δ ppm 3.724 (s, 3H), 3.829 (s, 2H), 4.069 (s, 3H), 7.139 (d, J=8.0 Hz, 1H), 7.465 (d, J=8.0 Hz, 1H).

Workup

  1. additionwere added
  2. concentrationconcentrated
  3. additionthe residue was diluted with water
  4. extractionextracted 2× with ethyl acetate
  5. washthe organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. additionDCM (40 mL) and excess 2M trimethylsilyldiazomethane in ether was added until the yellow color
  9. customthe excess was quenched with acetic acid
  10. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2b64c4c4b2084b2ba39e4d02d4eebaa3
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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