反応 #61854

反応方程式

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

収率 14.0%

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

収率 14.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他The 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
   その他the solvent was removed under reduced pressure
4. 4
   workup.ADDITIONthe resulting oil was diluted with ethyl acetate
5. 5
   洗浄washed with a saturated solution of sodium hydrogen carbonate, brine
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   その他the solvent removed under reduced pressure
9. 9
   その他to afford a brown oil
10. 10
    その他Purification by column chromatography

実験手順

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)+.

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