Tetrabutylammonium Fluoride → 5-(4-Chlorophenyl)-2-ethynyl-3-fluoropyridine

HRID 734800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734800
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([C:26]#[C:27][C:28]1[C:33]([F:34])=[CH:32][C:31]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[CH:30][N:29]=1)(C(C)(C)C)(C)C>C(Cl)Cl>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([C:31]2[CH:32]=[C:33]([F:34])[C:28]([C:27]#[CH:26])=[N:29][CH:30]=2)=[CH:36][CH:37]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 690583282-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine

Produkt 1

HCID 600554165-(4-Chlorophenyl)-2-ethynyl-3-fluoropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.14 g (3.61 mmol) of TBAF was added at RT to a solution of 1.25 g (3.61 mmol) of 2-[(tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine in 30 mL of DCM and the mixture was stirred for 2 hours. The organic phase was washed with water, dried over sodium sulfate, and evaporated down in vacuo. The residue was stirred with PE, the precipitate was filtered off, washed with PE, and dried in the air. Yield: 0.72 g (86% of theoretical); C13H7ClFN (M=231.653); calc.: molpeak (M+H)+: 232/234 (Cl); found: molpeak (M+H)+: 232/234 (Cl); HPLC-MS: 5.81 minutes (method B).

Aufarbeitung

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down in vacuo
  4. stirringThe residue was stirred with PE
  5. filtrationthe precipitate was filtered off
  6. washwashed with PE
  7. customdried in the air
  8. custom5.81 minutes (method B)

Quellen und Nachweise

ORD-Eintrag
ord-edf9bac4da0745ca9fd47e96455dba3f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592358B2

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