Reacción #61854

Ecuación de reacción

trifluoro-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methyl-oxazol-4-yl ester

1-naphthaleneboronic acid

potassium acetate

→

5-methyl-4-naphthalen-1-yl-oxazol-2-ylamine

Rendimiento 14.0%

5-Methyl-4-naphthalen-1-yl-oxazol-2-ylamine

Rendimiento 14.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed under reduced pressure and to the resulting yellow oil
2. 2
   workup.ADDITIONwas added dichloromethane (18 mL) and trifluoroacetic acid (2 mL)
3. 3
   Otrothe solvent was removed under reduced pressure
4. 4
   workup.ADDITIONthe resulting oil was diluted with ethyl acetate
5. 5
   Lavadowashed with a saturated solution of sodium hydrogen carbonate, brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe solvent removed under reduced pressure
9. 9
   Otroto afford a brown oil
10. 10
    OtroPurification by column chromatography

Procedimiento

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)+.

Fuente