HCID 67712379, compound → HCID 54287317, compound

HRID 1720218Notes

Reaction equation

HRID 1720218 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[C:11]#[C:12][Si](C)(C)C)[CH3:2]>CN(C=O)C.[F-].[K+].CCOCC>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[C:11]#[CH:12])[CH3:2]

Participants

5

Reactant 1

HCID 67712379HCID 67712379, compound

Product 1

HCID 54287317HCID 54287317, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 522689Potassium FluorideSolvent

Procedure

6.2 g of 2-(2'-trimethylsilylethynyl)-nicotinic acid ethyl ester are dissolved in 50 ml of DMF and 3 g of KF.2H2O are added. After stirring at RT, the reaction mixture is diluted with 300 ml of ether filtered through celite, shaken with 150 ml of water and refiltered. The aqueous phase is extracted four times with 100 ml ether and the combined ether extracts dried over MgSO4, filtered and dried under vacuum. The intermediate can be further purified by chromatography over silica with ethylacetate/hexane.

Workup

  1. addition2H2O are added
  2. filtrationfiltered through celite
  3. stirringshaken with 150 ml of water
  4. extractionThe aqueous phase is extracted four times with 100 ml ether
  5. dry with materialthe combined ether extracts dried over MgSO4
  6. filtrationfiltered
  7. customdried under vacuum
  8. customThe intermediate can be further purified by chromatography over silica with ethylacetate/hexane

Sources & evidence

ORD record
ord-72b1afcc417547f7ab17ab75324f9467
Source dataset
uspto-grants-1996_04
Patent number
US05506191

Reaction notes

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