反応 #608377

反応方程式

4-(cyanomethylidene)piperidinium chloride

X-Phos

4-bromo-1,2-dimethoxybenzene

Cs2CO3

Isocyanate

→

title compound

[1-(3,4-Dimethoxyphenyl)piperidin-4-ylidene]acetonitrile

溶媒

t-BuOH

反応条件

後処理

1. 1
   その他The reaction mixture was purged with argon for 5 minutes
2. 2
   その他the reaction flask was capped
3. 3
   温度The reaction was then cooled to ambient temperature
4. 4
   workup.ADDITIONdiluted with DMF
5. 5
   その他The mixture was then passed through a nylon syringe
6. 6
   ろ過filter (0.45 μm)
7. 7
   濃縮the filtrate was concentrated in vacuo

実験手順

In a sealed tube, 4-(cyanomethylidene)piperidinium chloride (16 mg, 0.10 mmol), Pd2(dba)3 (14 mg, 0.015 mmol), X-Phos (20 mg, 0.020 mmol), 4-bromo-1,2-dimethoxybenzene (33 mg, 0.15 mmol), and Cs2CO3 (98 mg, 0.30 mmol) were suspended in t-BuOH (0.5 mL). The reaction mixture was purged with argon for 5 minutes, the reaction flask was capped, and heated to 90° C. for 12 hours. The reaction was then cooled to ambient temperature and diluted with DMF:MeCN (1.0 mL, 50:50). To this mixture, Silica Supported-DMT (0.50 mmol, 0.57 mmol/g) followed by Silica Supported-Isocyanate (0.15 mmol, 1.33 mmol/g) was added. The resulting mixture was then shaken at 50° C. for 4 hours. The mixture was then passed through a nylon syringe filter (0.45 μm), and the filtrate was concentrated in vacuo to afford the title compound. The crude residue was used without further purification.

出典