反応 #327659

反応方程式

Sodium hydride

4-nitroindole

1-(t-Butyloxycarbonyl)-3-chloromethyl-7-azaindole

→

3-[(4-nitro-1H-indol-1-yl)methyl]-1H-pyrrolo[2,3-b]pyridine

収率 34.0%

溶媒

THF

反応条件

後処理

1. 1
   その他Upon completion (by TLC), the reaction was quenched with saturated aqueous ammonium chloride
2. 2
   その他The organic layer was separated
3. 3
   抽出the aqueous layer was extracted with ethyl acetate
4. 4
   洗浄The combined organic layers were washed with brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure to dryness
8. 8
   その他The residue was purified by flash column chromatography

実験手順

Sodium hydride (144 mg, 6 mmol) was added to a solution of 4-nitroindole (973 mg, 6 mmol) in THF, and the resulting mixture was stirred for 4 h. 1-(t-Butyloxycarbonyl)-3-chloromethyl-7-azaindole (Int-14, 1.5 g, 5.5 mmol) was then added. Upon completion (by TLC), the reaction was quenched with saturated aqueous ammonium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to dryness. The residue was purified by flash column chromatography to provide 3-[(4-nitro-1H-indol-1-yl)methyl]-1H-pyrrolo[2,3-b]pyridine (547 mg, 34%).

出典