Dichloromethane → HCID 178478048, Verbindung

HRID 2401737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401737
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[S:10][C:11]=2[C:12]2[N:16]=[CH:15][N:14](COCC[Si](C)(C)C)[N:13]=2)=[CH:4][CH:3]=1.C(Cl)Cl.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[S:10][C:11]=2[C:12]2[NH:16][CH:15]=[N:14][N:13]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 680066934-[4-(4-Chlorobenzyl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-thienyl]pyridine

Produkt 1

HCID 178478048HCID 178478048, VerbindungAusbeute 97 %

Versuchsvorschrift

The 4-[4-(4-chlorobenzyl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-thienyl]pyridine (58 mg, 0.12 mmol) and methylene chloride (4.0 mL, 62 mmol) were combined in a round bottomed flask equipped with a stirbar. The mixture was stirred and trifluoroacetic acid (1.1 mL, 14 mmol) was added in one portion. The resulting yellow solution was stirred overnight at rt under an atmosphere of nitrogen. Excess solvent was removed on the rotovap and the residue was digested in a mixture of EtOAc and aqueous sodium bicarbonate solution. The mixture was stirred then transferred to a separatory funnel. The organic layer was separated and the aqueous layer was extracted twice more with EtOAc. The organics were combined, washed with bicarbonate solution, then saline, and then dried over sodium sulfate. The mixture was filtered then evaporated in vacuo and the residue was purified by column chromatography on silica, elution 100% DCM to 100% EtOAc to afford the title compound as an off-white powder. Yield 41 mg (97% yield). LCMS: (FA) ES+, 353, 355. 1H NMR (400 MHz, d6-DMSO) δ: 14.31 (1H, br s), 8.67 (1H, br s), 8.55 (2H, d, J=6.3 Hz), 7.69 (1H, s), 7.63 (2H, d, J=6.3 Hz), 7.36-7.30 (4H, m), 4.47 (2H, s).

Aufarbeitung

  1. customequipped with a stirbar
  2. stirringThe resulting yellow solution was stirred overnight at rt under an atmosphere of nitrogen
  3. customExcess solvent was removed on the rotovap
  4. additionthe residue was digested in a mixture of EtOAc and aqueous sodium bicarbonate solution
  5. stirringThe mixture was stirred
  6. customthen transferred to a separatory funnel
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted twice more with EtOAc
  9. washwashed with bicarbonate solution
  10. dry with materialsaline, and then dried over sodium sulfate
  11. filtrationThe mixture was filtered
  12. customthen evaporated in vacuo
  13. customthe residue was purified by column chromatography on silica, elution 100% DCM to 100% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0a68296f29954f34ba506267672e1646
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796268B2

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