Ethyl Thioglycolate → HCID 57421980, compound

HRID 2108751Notes

Reaction equation

HRID 2108751 reaction equation
Cl/[C:2](/[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[CH:3]/[CH:4]=O.[SH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[O-]CC.[Na+]>CCO.CCOC(C)=O>[NH:8]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[C:6]([C:2]2[S:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=2)=[CH:7]1

Participants

6

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 57633205HCID 57633205, compound

Product 1

HCID 57421980HCID 57421980, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-3-chloro-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)acrylaldehyde (0.9 g. 4.3 mmol) was dissolved in EtOH (20 mL) and ethyl 2-mercaptoacetate (0.76 g, 6.3 mmol) and sodium ethoxide (1.0 g, 14.7 mmol) were added. The reaction mixture was heated to reflux for 90 minutes. The reaction mixture was diluted with EtOAc and the organic layer was washed with saturated sodium bicarbonate, dried over sodium sulfate, and concentrated to a solid, which was purified by column chromatography on silica (20 to 100% EtOAc/hexanes) to give the product, 890 mg, 3.3 mmol, 74% yield. 1H NMR 500 MHz (DMSO-d6) 12.19 (1H, br s), 8.32 (2H, m), 8.13 (1H, s), 7.78 (1H, d), 7.48 (1H, d), 7.23 (1H, dd), 4.31 (2H, q), 1.30 (3H, t).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 90 minutes
  3. washthe organic layer was washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a solid, which
  6. customwas purified by column chromatography on silica (20 to 100% EtOAc/hexanes)
  7. customto give the product, 890 mg, 3.3 mmol, 74% yield

Sources & evidence

ORD record
ord-ab9fd13cf3c942f5b7416bfd6fcf9d70
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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