反応 #45890

反応方程式

6-Amino-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

2,5-dimethoxytetrahydrofuran

→

compound

収率 81.0%

2-Cyclopropyl-7-fluoro-5-methyl-6-(pyrrol-1-yl)-1,3-benzoxazole-4-carbonitrile

収率 81.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   その他The solvent was evaporated away under reduced pressure
3. 3
   抽出The aqueous layer was further extracted twice with ethyl acetate
4. 4
   洗浄washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The insoluble matter was separated by filtration
7. 7
   その他the solvent was evaporated away
8. 8
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

実験手順

6-Amino-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-319) (29 mg, 0.13 mmol) was dissolved in acetic acid (2 ml), then at room temperature, 2,5-dimethoxytetrahydrofuran (49 μl, 0.38 mml) was added. The solution was stirred at 100° C. for 3 hours, then cooled to room temperature. The solvent was evaporated away under reduced pressure, the resulting residue was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=9:1, v/v) to obtain the entitled compound (28.5 mg, 81%) as a white solid.

出典