Tetrabutylammonium Fluoride → HCID 59852950, Verbindung

HRID 2374085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2374085
C[Si](C)(C)[C:3]#[C:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:4]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:7][CH:6]=1)#[CH:3]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 59853054Carbamic acid, [6-[(trimethylsilyl)ethynyl]-3-pyridinyl]-, 1,1-dimethylethyl ester

Produkt 1

HCID 59852950HCID 59852950, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 6-(2-(trimethylsilyl)ethynyl)pyridin-3-ylcarbamate (62 mg, 0.21 mmol) in THF (5 mL) was cooled to −15° C. and treated with 1.0 M tetrabutylammonium fluoride (Aldrich, 0.25 mL, 0.25 mmol) and stirred for 40 min. The mixture was concentrated in vacuo and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The EtOAc phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (45 mg, 100%) as an off-white solid. 1H NMR (DMSO-d6) δ 9.78 (s, 1H), 8.58 (d, 1H, J=2.5 Hz), 7.92-7.84 (m, 1H), 7.46 (d, 1H, J=8.6 Hz), 4.17 (s, 1H), 1.47 (s, 9H); MS(ESI+): m/z 219.20 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. washThe EtOAc phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-335dfbf8f30f44578eab1d0ea6fcfda0
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07459562B2

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