1-Naphthaleneboronic acid → 5-Methyl-4-naphthalen-1-yl-oxazol-2-ylamine

HRID 33576

Reaktionsgleichung

Reaktionsgleichung von HRID 33576
C(OC([NH:8][C:9]1[O:10][C:11]([CH3:22])=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]=1)=O)(C)(C)C.[C:23]1(B(O)O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[K+]>O1CCOCC1>[CH3:22][C:11]1[O:10][C:9]([NH2:8])=[N:13][C:12]=1[C:31]1[C:32]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 3

HCID 2545321-Naphthaleneboronic acidHCID 517044Potassium AcetateHCID 86590770Trifluoro-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methyl-oxazol-4-yl ester

Produkt 1

HCID 597968265-Methyl-4-naphthalen-1-yl-oxazol-2-ylamineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of trifluoro-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methyl-oxazol-4-yl ester (100 mg), 1-naphthaleneboronic acid (61 mg) palladium (0) tetrakis(triphenylphosphine) (17 mg), potassium acetate (85 mg) and 1,4-dioxane (5 mL) was heated at 180° C. for 24 hours. The solvent was removed under reduced pressure and to the resulting yellow oil was added dichloromethane (18 mL) and trifluoroacetic acid (2 mL). The mixture was stirred at room temperature for 1 hour and then the solvent was removed under reduced pressure, the resulting oil was diluted with ethyl acetate and washed with a saturated solution of sodium hydrogen carbonate, brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford a brown oil. Purification by column chromatography afforded 5-methyl-4-naphthalen-1-yl-oxazol-2-ylamine (30) (9 mg, 14%) as a white solid. 1H NMR (DMSO-D6): 2.15 (3H, s), 6.5 (2H, br s), 7.4-7.5 (4H, m), 7.85-7.90 (2H, m), 8.2 (1H, m). Mass Spectrum (m/z): 225 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure and to the resulting yellow oil
  2. additionwas added dichloromethane (18 mL) and trifluoroacetic acid (2 mL)
  3. customthe solvent was removed under reduced pressure
  4. additionthe resulting oil was diluted with ethyl acetate
  5. washwashed with a saturated solution of sodium hydrogen carbonate, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customto afford a brown oil
  10. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-82babac5748d4d23880cd6ea35080aee
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429607B2

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