Ethyl propiolate → pyrrolo[2,1-b]thiazole-7-carboxylic Acid Ethyl Ester

HRID 2064782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064782
F[C:2](F)(F)S(OC[Si](C)(C)C)(=O)=O.CS[C:16]1[S:17][CH:18]=[CH:19][N:20]=1.[CH2:21]([O:23][C:24](=[O:27])[C:25]#[CH:26])[CH3:22].[F-].[Cs+]>C(#N)C>[CH2:21]([O:23][C:24]([C:25]1[CH:26]=[CH:2][N:20]2[CH:19]=[CH:18][S:17][C:16]=12)=[O:27])[CH3:22]

Komponenten

6

Edukt 4

HCID 12182Ethyl propiolate2×HCID 25953Cesium fluorideHCID 27601002-(Methylthio)thiazoleHCID 2760857(Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent]

Produkt 1

HCID 23643153pyrrolo[2,1-b]thiazole-7-carboxylic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Under nitrogen atmosphere (trimethylsilyl)methyl trifluoromethanesulfonate (16.3 mmol) is added dropwise to a mixture of 2-methylthio-1,3-thiazole (15.5 mmol) in acetonitrile (75 mL). The mixture is treated with propynoic acid ethyl ester (23.2 mmol), kept with occasional shaking for 30 min at RT and added dropwise to a vigorously stirred solution of CsF (21.7 mmol) and propynoic acid ethyl ester (23.2 mmol) in acetonitrile (75 mL). After stirring for 1 h the mixture is concentrated in vacuo, diluted with DCM (100 mL), washed twice with water and twice with brine and dried over Na2SO4. The solvents are removed in vacuo and the residue is purified by flash chromatography (gradient: heptane to heptane/EtOAc 8/2) to give the desired product. LC-MS: tR=0.87 min; [M+H]+=196.0.

Aufarbeitung

  1. stirringAfter stirring for 1 h the mixture
  2. concentrationis concentrated in vacuo
  3. additiondiluted with DCM (100 mL)
  4. washwashed twice with water and twice with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvents are removed in vacuo
  7. customthe residue is purified by flash chromatography (gradient: heptane to heptane/EtOAc 8/2)

Quellen und Nachweise

ORD-Eintrag
ord-8d0639627b984ac89b6805ba2836ea34
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288435B2

Notizen zur Reaktion

Wird geladen…