Methyl iodide → HCID 11447978, Verbindung

HRID 1913368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913368
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[C:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=1.I[CH3:21]>C1COCC1>[CH3:21][N:12]([CH2:11][C:10]#[C:9][C:5]1[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=1)[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70832777tert-Butyl [3-(pyridin-3-yl)prop-2-yn-1-yl]carbamate

Produkt 1

HCID 11447978HCID 11447978, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of sodium hydride (60% dispersion in mineral oil, 30 mg, 0.95 mmol) in anhydrous THF (3 mL) at 0° C. was added a solution of 47 (109 mg, 0.47 mmol) in anhydrous THF (2 mL) dropwise over 15 min. To the resultant solution was added a solution of iodomethane (150 μL, 2.42 mmol) in THF (5 mL) over 10 min, the ice bath was removed and the solution was stirred at ambient temperature for 16 h. The reaction was stopped by the addition of water (5 mL) and the aqueous fraction was extracted with EtOAc (3×20 mL), washed with water, dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.18) to afford the title compound 49 (69 mg, 60% yield) as a yellow oil: 1H NMR (CDCl3) δ 8.65 (s, 1H), 8.52 (m, 1H), 7.69 (m, 1H), 7.24 (m, 1H), 4.29 (s, 2H), 2.97 (s, 3H), 2.97 (s, 9H); LRMS (ESI) m/z calcd for C14H19N2O2 [M H]+ 247. found 247.

Aufarbeitung

  1. customthe ice bath was removed
  2. additionThe reaction was stopped by the addition of water (5 mL)
  3. extractionthe aqueous fraction was extracted with EtOAc (3×20 mL)
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.18)

Quellen und Nachweise

ORD-Eintrag
ord-7c66ec7664fc45c2b2e23ff3918182ca
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609708B2

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